Arthropodicidal oxazolines and thiazolines

ABSTRACT

Arthropodicidally active compounds, compositions and a method for using them, the compounds having the formula ##STR1## wherein A, Q, Z, (E) q , R 1  and R 2  are as defined in the text.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation in part of application Ser. No.08/338,500 filed Nov. 22, 1994, now abandoned which is a continuation ofapplication Ser. No. 08/024,576 filed Mar. 1, 1993, now abandoned, whichis a continuation of application Ser. No. 07/956,927 filed Oct. 5, 1992,now abandoned which is a continuation of application Ser. No. 07/889,026filed May 26, 1992 now abandoned.

BACKGROUND OF THE INVENTION

The arthropodicidal and acaricidal oxazolines and thiazolines of thisinvention are characterized by a fused ring system or a monocyclicheterocycle. This ring distinguishes the compounds of this inventionfrom those of EP 345,775 and EP 432,661. N. Ardabilchi, et al., J. Chem.Soc, Perkin Trans I (1979), 539-543 discloses4,5-dihydro-4-methyl-5-(1-naphthalenyl)-2-phenyloxazole but does notdisclose any arthropodicidal utility.

SUMMARY OF THE INVENTION

The invention pertains to compounds of Formula I, including allgeometric and stereoisomers, agriculturally suitable salts thereof,agricultural compositions containing them and their use asarthropodicides and acaricides in both agronomic and nonagronomicenvironments. The compounds are ##STR2## wherein: A is selected from thegroup a direct bond and C₁ -C₃ straight or branched chain alkylene;

E is selected from the group C₁ -C₄ alkyl and C₁ -C₄ haloalkyl;

Z is selected from the group O and S;

q is 0, 1, 2 or 3;

Q is a 5- to 16- membered aromatic ring system selected from the group:

(i) monocylic aromatic ring containing 1 to 4 heteroatoms independentlyselected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur; p2(ii) fused carbobicyclic ring containing 8 to 12 carbons, with theproviso that when the ring is naphthyl and is on the oxazoline ringcarbon adjacent to the oxazoline ring oxygen, and when E is CH₃ and q is1, then R¹ is other than H;

(iii) fused carbotricyclic ring containing 12 to 16 carbons;

(iv) fused bicylic ring containing 1 to 4 heteroatoms independentlyselected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur;

(v) fused tricylic ring containing 1 to 6 heteroatoms independentlyselected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur; and

(vi) phenyl substituted with M-J¹ ;

Q being substituted with I to 6 substituents selected independently fromthe group R³, R⁴, (R⁵)_(p) and (R⁶)_(m) ;

R¹ and R² are independently selected from the group H, halogen, C₁ -C₆alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy, C_(1-C) ₆ alkylthio, CN andNO₂ ;

R³ and R⁵ are independently selected from the group H, halogen, C₁ -C₁₆alkyl, C₁ -C₁₆ haloalkyl, C₃ -C₇ cycloalkyl, C₄ -C₁₆ cycloalkylalkyl, C₂-C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl, C₂ -C₁₆ alkynyl, C₂ -C₁₆ haloalkynyl,C₂ -C₁₆ alkoxyalkoxy, OR⁷, R⁷ OC(O)--, R₇ C(O)--, Si(R¹³)(R¹⁴)R¹⁵ andM-J;

R⁴ is selected from the group H, halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy,C₁ -C₆ haloalkyl and C₁ -C₆ haloalkoxy;

R⁶ is selected from the group H, halogen, C₁ -C₁₀ alkyl, C₁ -C₆ alkoxy,C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy; and phenyl optionally substitutedwith R⁸ ;

R⁷ is selected from the group C₃ -C₇ cycloalkyl, C₄ -C₇ cycloalkylalkyl,C₁ -C₁₆ alkyl, C₁ -C₁₆ haloalkyl, C₂ -C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl,C₂ -C₁₆ alkynyl and C₂ -C₁₆ haloalkynyl;

R⁸ is selected from the group halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁-C₆ haloalkyl, C₁ -C₆ haloalkoxy and Si(R⁹)(R¹⁰)R¹¹ ;

R⁹, R¹⁰ and R¹¹ are independently C₁ -C₁₂ alkyl;

M is selected from the group a direct bond, S, O, C(═O), C(═O)O--C₁ -C₂alkylene, C₁ -C₄ alkylene, O--C₁ -C₄ alkylene and O--C₂ -C₄ alkenylene,wherein when M is O--C₁ -C₄ alkylene or O--C₂ -C₄ alkenylene, the oxygenatom is attached to either ring and when M is C(═O)O--C₁ -C₂, the C(═O)is attached to either ring;

J is selected from the group phenyl optionally substituted withindependently selected substituents (R¹²)_(n) ; and a 5-or 6-memberedaromatic ring, attached through carbon or nitrogen, containing 1 to 4heteroatoms independently selected from the group 0-4 nitrogen, 0-1oxygen, and 0-1 sulfur, the ring optionally substituted withindependently selected substituents (R¹²)_(n) ;

J¹ is selected from the group a 5- membered aromatic ring, attachedthrough carbon or nitrogen, containing 1 to 4 heteroatoms independentlyselected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur, and a6-membered ring containing 2 to 4 nitrogen atoms each ring optionallysubstituted with independently selected substituents (R¹²)_(n) ;

R¹² is selected from the group halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁-C₆ haloalkyl, C₁ -C₆ haloalkoxy and Si(R¹³)(R¹⁴)R¹⁵ ;

R¹³, R¹⁴ and R¹⁵ are independently C₁ -C₁₂ alkyl;

m and n are integers independently selected from 1 to 4; and

p is 1 or 2.

Preferred Compounds A are compounds of Formula I wherein Q is selectedfrom the group: ##STR3## G being selected from the group O and S; W, Xand Y being independently selected from the group N, S, O, CR⁵, N═CR⁶and NR¹⁶ wherein only one of W, X and Y is O, S or N═CR⁶ ;

R¹⁶ being selected from the group H, C₁ -C₆ alkyl and phenyl optionallysubstituted with 1 to 3 substituents independently selected from thegroup R¹⁷ ;

R¹⁷ is selected from the group C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, halogen,NO₂ and CN; and

t is 1, 2 or 3.

Preferred compounds of this invention are those wherein Q is selectedfrom the group ##STR4## A is selected from the group a direct bond andC₁ -C₃ straight or branched chain alkylene;

G and Z are independently selected from the group O and S;

W, X and Y are independently selected from the group S, O, CR³, N═CR⁷and NR⁸ wherein only one of W, X and Y can be O, S or N═CR⁷ ;

R¹ and R² are independently selected from the group H, halogen, C₁ -C₆alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy, C₁ -C₆ alkylthio, CN and NO₂;

R³ and R⁵ are independently selected from the group H, halogen, C₁ -C₁₆alkyl, C₃ -C₇ cycloalkyl, C₄ -C₁₆ cycloalkylalkyl, C₁ -C₁₆ haloalkyl, C₂-C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl, C₂ -C₁₆ alkynyl, C₂ -C₁₆ haloalkynyl,C₂ -C₁₆ alkoxyalkoxy, OR⁹, R⁹ OC(O)--, R⁹ C(O)-- and ##STR5## R⁴ and R⁷are independently selected from the group H, halogen, C₁ -C₆ alkyl, C₁-C₆ alkoxy, C₁ -C₆ haloalkyl and C₁ -C₆ haloalkoxy;

R⁶ is selected from the group H, halogen, C₁ -C₁₀ alkyl and phenyloptionally substituted with R¹⁰ ;

R⁸ is selected from the group H and C₁ -C₆ alkyl;

R⁹ is selected from the group C₃ -C₇ cycloalkyl, C₄ -C₇ cycloalkylalkyl,C₁ -C₁₆ alkyl, C₁ -C₁₆ haloalkyl, C₂ -C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl,C₂ -C₁₆ alkynyl and C₂ -C₁₆ haloalkynyl;

R¹⁰ is selected from the group halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁-C₆ haloalkyl, C₁ -C₆ haloalkoxy and Si(R¹¹) (R¹²)R¹³ ;

R¹¹, R¹² and R¹³ are independently C₁ -C₃ alkyl;

J is selected from the group CH, CR¹⁰ and N;

M is selected from the group a direct bond, O, C(O), C(O)O and C₁ -C₃straight or branched chain alkylene;

m is an integer from 1 to 4;

n is 0 or an integer from 1 to 4;

p is 1 or 2;

t is 1, 2 or 3; and

q is 0.

Preferred Compounds B are Compounds A wherein where one of W, X or Y isS, the remaining two are not both CR⁵.

Preferred Compounds C are Compounds A wherein:

A is a direct bond;

R¹ is selected from the group F and Cl in the 2-position;

R² is selected from the group H, F and Cl in the 6-position;

R³ and R⁵ are independently selected from the group H, halogen, C₁ -C₆alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy and M-J; and

J is selected from the group phenyl, thienyl, pyridyl and furyl.

Preferred Compounds D are Compounds C wherein Q is selected from thegroup Q-1, Q-2, Q-3 and Q-4.

Preferred Compounds E are Compounds D wherein:

Q is Q-1;

W is S;

X and Y are CR⁵ ;

R³ is M-J;

M is a direct bond;

J is phenyl;

R¹² is in the meta or para position and is selected from the grouphalogen and CF₃ ; and

n is 1 or 2.

Preferred Compound F is the compound of Preferred D which is:

(2-(2,6-difluorophenyl)-4-[5-(1,1-dimethylethyl)-2-thienyl]-4,5-dihydrooxazole.

Preferred Compound G is the compound of Preferred D which is:

2-(2,6-difluorophenyl)-4-(2,2-dimethyl-1,3-benzodioxol-5-yl)-4,5-dihydrooxazole.

Preferred Compound H is the compound of Preferred E which is:

4-[5-(4-chlorophenyl)-2-thienyl]-2-2-(2,6-difluorophenyl)-4,5-dihydrooxazole.

The invention also pertains to a method for controlling arthropodscomprising applying to the arthropods or their environment anarthropodicidally effective amount of a compound of Formula IA ##STR6##wherein: A is selected from the group a direct bond and C₁ -C₃ straightor branched chain alkylene;

E is selected from the group C₁ -C₄ alkyl and C₁ -C₄ haloalkyl;

Z is selected from the group O and S;

q is 0, 1, 2 or 3;

Q is a 5- to 16- membered aromatic ring system selected from the group:

(i) monocylic aromatic ring containing 1 to 4 heteroatoms independentlyselected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur;

(ii) fused carbobicyclic ring containing 8 to 12 carbons;

(iii) fused carbotricyclic ring containing 12 to 16 carbons;

(iv) fused bicylic ring containing 1 to 4 heteroatoms independentlyselected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur;

(v) fused tricylic ring containing 1 to 6 heteroatoms independentlyselected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur; and

(vi) phenyl substituted with M-J¹ ;

Q being substituted with 1 to 6 substituents selected independently fromthe group R³, R⁴, (R⁵)_(p) and (R⁶)_(m) ;

R¹ and R² are independently selected from the group H, halogen, C₁ -C₆alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy, C₁ -C₆ alkylthio, CN and NO₂;

R³ and R⁵ are independently selected from the group H, halogen, C₁ -C₁₆alkyl, C₁ -C₁₆ haloalkyl, C₃ -C₇ cycloalkyl, C₄ -C₁₆ cycloalkylalkyl, C₂-C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl, C₂ -C₁₆ alkynyl, C₂ -C₁₆ haloalkynyl,C₂ -C₁₆ alkoxyalkoxy, OR⁷, R⁷ OC(O)--, R⁷ C(O)--, Si(R¹³)(R¹⁴)R¹⁵ andM-J;

R⁴ is selected from the group H, halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy,C₁ -C₆ haloalkyl and C₁ -C₆ haloalkoxy;

R⁶ is selected from the group H, halogen, C₁ -C₁₀ alkyl, C₁ -C₆ alkoxy,C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy; and phenyl optionally substitutedwith R⁸ ;

R⁷ is selected from the group C₃ -C₇ cycloalkyl, C₄ -C₇ cycloalkylalkyl,C₁ -C₁₆ alkyl, C₁ -C₁₆ haloalkyl, C₂ -C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl,C₂ -C₁₆ alkynyl and C₂ -C₁₆ haloalkynyl;

R⁸ is selected from the group halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁-C₆ haloalkyl, C₁ -C₆ haloalkoxy and Si(R⁹)(R¹⁰)R¹¹ ;

R⁹, R¹⁰ and R¹¹ are independently C₁ -C₁₂ alkyl;

M is selected from the group a direct bond, S, O, C(═O), C(═O)O--C₁ -C₂alkylene, C₁ -C₄ alkylene, O--C₁ -C₄ alkylene and O--C₂ -C₄ alkenylene,wherein when M is O--C₁ -C₄ alkylene or O--C₂ -C₄ alkenylene, the oxygenatom is attached to either ring and when M is C(═O)O--C₁ -C₂, the C(═O)is attached to either ring;

J is selected from the group phenyl optionally substituted withindependently selected substituents (R¹²)_(n) ; and a 5-or 6-memberedaromatic ring, attached through carbon or nitrogen, containing 1 to 4heteroatoms independently selected from the group 0-4 nitrogen, 0-1oxygen, and 0-1 sulfur, the ring optionally substituted withindependently selected substituents (R¹²)_(n) ;

J¹ is selected from the group a 5- membered aromatic ring, attachedthrough carbon or nitrogen, containing 1 to 4 heteroatoms independentlyselected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur, and a6-membered ring containing 2 to 4 nitrogen atoms each ring optionallysubstituted with independently selected substituents (R¹²)_(n) ;

R¹² is selected from the group halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁-C₆ haloalkyl, C₁ -C₆ haloalkoxy and Si(R¹³)(R¹⁴)R¹⁵ ;

R¹³, R¹⁴ and R¹⁵ are independently C₁ -C₁₂ alkyl;

m and n are integers independently selected from 1 to 4; and

p is 1 or 2.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers and geometricisomers. One skilled in the art will appreciate that one stereoisomermay be more active than the others and how to separate stereoisomers.Accordingly, the present invention comprises racemic mixtures,individual stereoisomers, and optically active mixtures of compounds ofFormula I as well as agriculturally suitable salts thereof.

The term "aromatic ring system" is defined as those ring systems whichsatisfy the Hackel rule, examples include: (i) a 5- or 6- memberedmonocyclic aromatic ring containing 1 to 4 heteroatoms such as furyl,furazanyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, oxadiazolyl,imidazolyl, isoxazolyl, thiazolyl, thiadiazolyl isothiazolyl,tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl and triazinylwith said ring attached through any available carbon or nitrogen, forexample, when the aromatic ring system is furyl, it can be 2-furyl or3-furyl, for pyrrolyl, the aromatic ring system is 1-pyrrolyl,2-pyrrolyl or 3-pyrrolyl, for pyridyl, the aromatic ring system is2-pyridyl, 3-pyridyl or 4-pyridyl and similarly for other monocyclicaromatic rings; (ii) fused carbobicyclic ring containing at least onephenyl ring, examples include naphthyl and tetralinyl; (iii) fusedcarbotricylic ring containing at least one phenyl ring, examples includefluorenyl and phenanthrenyl; (iv) fused bicyclic rings containing 1 to 4heteroatoms and 1 or 2 aromatic rings, examples include quinolyl,isoquinolyl, quinoxalinyl, benzofuryl, isobenzofuranyl, benzothienyl,benzodioxolyl, chromanyl, indolinyl, isoindolyl, thienofuranyl, andpurinyl; and (v) fused tricyclic rings containing 1 to 6 heteroatoms andat least 1 aromatic ring, examples include acridinyl, phenanthridinyl,phenanthrolinyl, phenoxazinyl, and dibenzofuranyl. As with themonocyclic aromatic rings, the bicyclic and tricyclic aromatic ringsystems can be attached through any available carbon or nitrogen, forexample, for naphthyl, the carbobicyclic aromatic ring system is1-naphthyl or 2-naphthyl, for benzofuryl, the aromatic ring system canbe ,2-, 3-, 4-, 5-, 6-, or 7-benzofuryl, for fluorenyl, the aromaticring system can be 1-, 2-, 3-, 4-, or 9-fluorenyl and similarly for theother bicyclic and tricyclic aromatic ring systems. Q-1 is an example ofaromatic ring system (i); Q-3 and Q-7 of ring system (ii); Q-2, Q-4, Q-5and Q-6 of ring system (iv); Q-8 of ring system (v); and Q-9 of ringsystem (vi).

In the above recitations, the term "alkyl" used either alone or incompound words such as "alkylthio" or "haloalkyl", denotes straight orbranched alkyl such as methyl, ethyl, n-propyl, isopropyl and thedifferent butyl, pentyl and hexyl isomers. Alkylene and alkenylenedenote both straight and branch chains.

Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and thedifferent butoxy, pentoxy and hexyloxy isomers. Alkenyl denotes straightor branched chain alkenes such as vinyl, 1-propenyl, 2-propenyl and thedifferent butenyl, pentenyl and hexenyl isomers. Alkynyl denotesstraight chain or branched alkynes such as ethynyl, 1-propynyl,3-propynyl and the different butynyl, pentynyl and hexynyl isomers.Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.The term "halogen", either alone or in compound word such as"haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as "haloalkyl", said alkyl can bepartially or fully substituted with independently selected halogenatoms. Examples of haloalkyl include CH₂ CH₂ F, CF₂ CF₃ and CH₂ CHFCl.The terms "haloalkenyl" and "haloalkynyl" are defined analogously to theterm "haloalkyl".

The total number of carbon atoms in a substituent group is indicated bythe "C_(i) -C_(j) " prefix where i and j are numbers from 1 to 16. Forexample, C₄ alkoxyalkoxy designates the various isomers of an alkoxygroup substituted with a second alkoxy group containing a total of 4carbon atoms, examples including OCH₂ OCH₂ CH₂ CH₃ and OCH₂ CH₂ OCH₂CH₃.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents.

DETAILS OF THE INVENTION

Compounds of Formula I can be made from amino alcohols (or thiols) ofFormula II and benzoic acid derivatives as shown in Scheme 1. Thetransformation generally consists of two steps. First, the compound ofFormula II is condensed with the benzoic acid derivative to form anamide of Formula III. A generally useful way to do this is to treat thecompound of Formula II with an aroyl chloride in the presence of an acidacceptor (usually a tertiary amine base such as triethylamine) at roomtemperature or below. This reaction can be carried out in an inertsolvent such as dichloromethane, tetrahydrofuran, toluene, and othersolvents that will not react with acid chlorides or bases. There areother useful ways to form amides, many examples of which are found inLarock, "Comprehensive Organic Transformations," VCH Publishers, Inc.,New York, pp. 972-981). The second step carried out is the ring closure.This can be accomplished by treating the intermediate amide of FormulaIII with a dehydrating agent. Some useful reagent systems for thistransformation include but are not limited to triphenyl phosphine/carbontetrachloride, diethylazodicarboxylate/triphenyl phosphine, and thionylchloride. An especially useful method for ring closure involvestreatment of the amide with thionyl chloride in benzene or other inertsolvent at reflux until the starting material is consumed. The residueof this reaction is treated with an inorganic base such as sodium orpotassium hydroxide in an alcoholic or aqueous medium. Many methods forring closure to oxazolines have been compiled by Frump (Chemical Rev.(1971), 71, 483-505). ##STR7##

Alternatively, compounds of Formula III (where A is a direct bond) canbe prepared in two steps as shown in Scheme 2. First, compounds ofFormula IV are amidoalkylated with a compound of Formula V to formFormula VI compounds. A typical reaction involves the combination ofcompounds of Formulae IV and V in an acid such as sulfuric acid,methanesulfonic acid, trifluoroacetic acid, polyphosphoric acid andperchloric acid. The reaction can be run in a cosolvent such as aceticacid. The reaction temperature can range from -10° to 200° C. with0°-100° C. being preferred. Alternatively, the reaction can be carriedout in an inert solvent such as chloroform, methylene chloride, benzene,toluene and ether in the presence of a Lewis acid such as aluminumchloride or boron trifluoride. Amidoalkylation reactions have beenextensively reviewed in the literature (see Zaugg, Synthesis (1984),85-110). The second step is the reduction of a Formula VI compound toform a Formula III compound. Reductions of this type are well-known inthe art (see Hudlicky, Reductions in Organic Chemistry (1984), 136-163).Typical reducing agents include the alkali metal borohydrides anddiborane. ##STR8##

The preparation of Formula V compounds can be accomplished by refluxingglyoxylic acid derivatives (Formula VII) and commercially availablebenzamides (Formula VIII) in an inert solvent such as acetone, benzeneand chloroform (Scheme 3). This procedure is known in the art (seeBen-Ishai, Tetrahedron (1975), 31, 863-866 and Tetrahedron (1977), 33,881-883). ##STR9##

As shown in Scheme 4, amino alcohols of Formula II can be produced bythe treatment of an amino acid derivative of Formula IX with a reducingagent. In the reduction process, aminoesters are preferred, but aminoacids themselves can also be used. There are many reagents known toreduce acids and esters to alcohols. (See Larock, loc. cit., pp.548-553). Particularly useful are alkali metal hydrides and boranes. Forexample, treatment of a compound of Formula IX with lithium aluminumhydride at 0°-50° C. in ethereal solvents such as tetrahydrofuran,ether, or dimethoxyethane gives an alcohol of Formula II. ##STR10##

As shown in Scheme 5, amino alcohols of Formula II can be produced bythe direct reduction of oximo acids and esters of Formula X with boranesor alkali metal hydrides. The reaction conditions with lithium aluminumhydride are as described for Scheme 4. ##STR11##

Aryl-substituted amino acids and esters of Formula IX are known in theart as are methods for their preparation. Useful compendia of methodsfor their synthesis are contained in Kukolja (J. Med. Chem. (1985), 28,1886-1896), Bohme (J. Med. Chem. (1980), 23,405-412), and O'Donnell(Tetrahedron Lett. (1989), 30, 3909-3912) and references cited within.

Oximo esters of Formula X are especially suitable intermediates for thesynthesis of compounds of Formula I. They can be made from aryl aceticesters of Formula XI by reaction, in the presence of base, withnitrosating agents such as inorganic and organic nitrites as shown inScheme 6. Typically, the compound of Formula VI is treated with an alkylnitrite such as butyl nitrite in an alcoholic solvent such as ethanol inthe presence of a strong base such as sodium ethoxide at the refluxtemperature of the solvent. ##STR12##

Alternatively, as shown in Scheme 7, compounds of Formula X can beproduced from aryl glyoxalates of Formula XII by treatment with aderivative of hydroxylamine. Aryl glyoxalates can be made by thereaction of an organometallic species with a derivative of oxalic acid.For instance, diethyl oxalate can be treated with an aryl Grignardreagent at low temperature in ether/tetrahydrofuran mixtures (Rambaud,et al., Synthesis (1988), 564-567). ##STR13##

Another method for the synthesis of compounds of Formula XII, shown inScheme 8, is by use of the Friedel-Crafts reaction. Monoesters of oxalylchloride react with electron-rich aromatics of Formula XIII in thepresence of Lewis acids to give compounds of Formula XII. See Olah ed.,"Friedel-Crafts and Related Reactions," Vol. 3, Part 1, pp. 1-16.Treatment of compounds of Formula XIII with aluminum chloride and ethylor methyloxalyl chloride in an inert solvent such as dichloromethane,nitrobenzene, carbon disulfide, or dichloroethane will produce compoundsof Formula XII. ##STR14##

Compounds of the instant invention where Q is phenyl substituted withM-J¹ can be made by methods known in the art. As shown in Scheme 9,compounds of Formula XIII substituted by a halogen or triflate can becoupled with heterocyclic compounds of Formula XIV containing tin, zinc,boron, magnesium, lithium, or other metal in the presence of a nickel orpalladium catalyst to give compounds of the present invention where M isa direct bond or an alkylene group. Methods and conditions for thespecific introduction of heterocyclic compounds under these conditionscan be found in Kalinin, Synthesis, (1992), 413-432. ##STR15##

As shown in Scheme 10, compounds of Formula I where Q is phenyl and M iseither O, S, or O-alkylene can be made by alkylation chemistry.Compounds of Formula XV where Q is phenyl substituted or OH or SH can betreated with a heterocycle of Formula XVI containing a leaving group(halogen, sulfonate, or sulfone for example) in the presence of an acidacceptor. The transformation is best carried out in an aprotic dipolarsolvent such as dimethylformamide or dimethylacetamide. Depending on thereactivity of the heterocycle and the nature of the leaving group, avariety of acid acceptors and temperatures can be utilized. Somesuitable bases am potassium carbonate, potassium-t-butoxide, and sodiumhydride. ##STR16##

Compounds of Formula IV are known in the art. Heterocyclic compounds ofFormula IV where Q=Q-1, Q-5, Q-6, and Q-8 are known and methods for thepreparation of these compounds as well as compounds of Formula XIV andXVI can be found in Katritsky and Rees eds., "Comprehensive HeterocyclicChemistry" Vol. 2-6, Pergamon Press, New York, (1984) and in Coffey ed.,"Rodd's Chemistry of Carbon Compounds" Vol. IVa-1, Elsevier, Amsterdam,(1973-1980).

Compounds of Formula IV where Q=Q-2, Q-3, and Q-4 are also known.Methods for synthesis of these compounds can be found in European PatentApplication 350,846; Berlin el. al., J. Med. Chem., (1985) 28, 116-124;Dawson et al., J. Med. Chem., (1984), 27, 1516-1531; and Olah, loc.cit., Vol. 2, 785-952. Compounds of Formula IV where Q=Q-7 are known anda review of the chemistry and synthesis of naphthalenes can be found inCoffey, loc. cit., Vol. IIIg, 99-284. These references also includefunctional group manipulations of the various Q groups which one skilledin the art can use to convert compounds of the instant invention toother compounds of the instant invention.

It is recognized that in many of the transformations described, it isnecessary to utilize appropriate protecting groups to prevent unwantedside reactions or use reagents that do not affect functional groupsother than those desired to be changed. One skilled in the art will beable to select appropriate protecting groups and reagents to this end.

EXAMPLE 1

2-(2,6-difluorophenyl)-4,5-dihydro-4-(2-naphthalenyl)-oxazole

Ethyl 2-naphthylacetate (11.6 g) was dissolved in ethanol (100 mL) andtreated with solid sodium ethoxide (3.5 g) and then dropwise withn-butyl nitrite (7.6 mL). The reaction was stirred at 23° C. for 18 hand treated with acetic acid (5 mL) and stirred for 1 h. The ethanol wasremoved under reduced pressure and the residue was partitioned betweenethyl acetate and water. The organic phase was dried over magnesiumsulfate and evaporated under reduced pressure. The residue waschromatographed on silica gel with hexanes/ethyl acetate (5:1 to 3:1) aseluent. The crude residue (5.6 g) was taken up in ether (300 mL) cooledto 0° C. and treated with lithium aluminum hydride solution (45 mL, 1Min tetrahydrofuran) dropwise. The mixture was heated to reflux for 5 hand cooled. It was quenched by the sequential addition of ethyl acetate(5 mL) water (1.5 mL), sodium hydroxide solution (3M, 1.5 mL) and water(4 mL). The solid was filtered and the solution was dried with magnesiumsulfate. The solvent was removed at reduced pressure and the solid wastriturated with hexanes/butyl chloride (1:1, 100 mL). Of the crude2-naphthylglycinol (2.6 g) thus obtained, 1.2 g was dissolved intetrahydrofuran and treated with triethylamine (1 mL) and cooled in anice water bath. Treatment of the mixture with 2,6-difluorobenzoylchloride (1 mL) was followed by stirring at room temperature for 1 h.The mixture was diluted with dichloromethane and water. The organicphase was washed sequentially with sodium bicarbonate solution(saturated aqueous) and 1N hydrochloric acid. The solvent was dried withmagnesium sulfate and removed under reduced pressure. The residue waschromatographed on silica gel with hexanes/ethyl acetate (5:1 to 1:1) aseluent. The product was treated with benzene (20 mL), thionyl chloride(3 mL) was added and the mixture heated at reflux for 2.5 h. The solventwas removed under reduced pressure and the residue was treated withmethanol (20 mL) and NaOH (50% aqueous, 1.5 mL), and heated at refluxfor 1 h. The mixture was evaporated under reduced pressure and theresidue was partitioned between water and ethyl acetate. The ethylacetate layer was dried over magnesium sulfate and evaporated underreduced pressure. The residue was chromatographed on silica gel usinghexanes/ethyl acetate (5:1) as eluent to afford the title compound (0.68g) as an oil which quickly solidified: mp 68°-70° C., ¹ H NMR (CDCl₃):15 8.0-7.0 (m,10H, aryl H), 5.6 (m, 1H,CH), 4.9 (m, 1H,CH), 4.4 (m,1H,CH).

EXAMPLE 2

Step A: [(2,6-difluorobenzoyl)amino]hydroxyacetic acid

A mixture of 50 g (0.318 mol) of 2,6-difluorobenzamide, 32 g (0.349 mol)of glyoxylic acid monohydrate and 200 mL of acetone was refluxed for 5h. The reaction was cooled and solvents evaporated to give a whitesolid. It was triturated with cold acetone to afford 38.56 g of a whitesolid: mp 125°-127° C. ¹ H-NMR (DMSO-d₆)δ9.55 (d, 1H), 7.50 (m, 1H),7.15 (t,2H), 5.45 (d,1H)

Step B: 5-bromo-α-[(2,6-difluorobenzoyl)amino]2-thiopheneacetic acid

A solution of 4.76 g (20.6 mmol) of the product of Step A in 140 mL ofmethanesulfonic acid was immersed in an ice-water bath (temperaturebetween 5°-10° C.). Then, 4.0 g (24.6 mmol) of 2-bromothiophene wasadded dropwise. It was stirred at the same temperature until a deepblue-black color formed. It was poured into ice-water and the resultingprecipitate was filtered. The solid was triturated with methylenechloride to give 4.05 g of a tan solid: mp 198°-199° C. (dec.). ¹ H-NMR(DMSO-d6) δ9.80 (d,1H), 7.55 (m, 1H), 7.20 (m,3H), 7.00 (d, 1H), 5.80(d, 1H).

Step C: Methyl 5-bromo-α-[(2,6-difluorobenzoyl)amino]2-thiopheneacetate

An amount of 3.415 g (9 mmol) of the product of Step B was dissolved in19 mL of methanol. It was cooled in an ice-bath and 1.13 mL of thionylchloride was added dropwise. The mixture was heated at reflux for 30min. It was cooled and the methanol removed under reduced pressure. Asaturated solution of sodium bicarbonate was carefully added to theresidue, then extracted with ether. The combined ether extracts werewashed with brine, dried (MgSO₄) and concentrated to give a white solid:mp 123°-124° C. ¹ H-NMR (DMSO-d6) δ9.90 (d, 1H), 7.55 (m, 1H), 7.20(m,3H), 7.00 (d, 1H), 5.90 (d, 1H), 3.75 (s,3H).

Step D: 4-(5-bromo-2-thienyl)-2-(2,6-difluorophenyl)4,5-dihydrooxazole

An amount of 830 g (7.5 mmol) of anhydrous calcium chloride, 565 mg (15mmol) of sodium borohydride and 15 mL of dry THF was stirred for 1 h. Tothis mixture was added 1.96 g (5 mmol) of the product of Step C in 10 mLof dry THF all at once. The resulting mixture was stirred at roomtemperature for 2 h. The reaction was immersed in an ice-bath andcarefully quenched with 5% HCl and extracted with ethyl acetate. Thecombined ethyl acetate extracts were washed with brine, dried (MgSO₄)and concentrated to give 270 mg of a white solid. To a mixture of thesolid, 111 mg(1.1 mmol) of triethylamine, 0.68 mL of carbontetrachloride and 3.5 mL of acetonitrile was added 289 mg(1.1 mmol) oftriphenylphosphine. The mixture was stirred at room temperature for 35min. Solids were filtered and the residue washed several times withcarbon tetrachloride. The combined filtrate and washings wereconcentrated. The residue was purified by passing through a silica gelflash column eluting with ethyl acetate: hexanes (1:2) to give an oil. ¹H-NMR (DMSO-d6) δ7.70 (m, 1H), 7.30 (t,2H), 7.15 (d, 1H), 6.95 (d, 1H),5.70 (dd, 1H), 4.80 (t, 1H), 4.35 (t, 1H).

EXAMPLE 3

2-(2,6-difluorophenyl)-4,5-dihydro-4-(5-phenyl-2-thienyl)oxazole

To a solution of 100 mg (0.3 mmol) of the product of Step D of Example 2in 0.6 mL toluene was added successively 10.4 mg (0.009 mmol) of Pd(PPh₃)₄, 0.3 mL of 2.0 m sodium carbonate, and 44 mg (0.36 mmol) ofphenylboronic acid in 0.15 mL of methanol. The mixture was stirred at80° C. for 2 h. It was cooled and partitioned between 25 mL of 2.0 msodium carbonate containing 2.5 mL of ammonium hydroxide solution and 25mL of methylene chloride. The methylene chloride layer was washed withbrine, dried (MgSO₄), and concentrated. The residue was passed through asilica gel flash column eluting with ethyl acetate: hexanes (1:4) togive 85 mg of an oil. ¹ H-NMR (CDCl₃) δ6.90-7.20 (m, 10H), 5.70 (dd,1H),4.80 (t, 1H), 4.45 (t, 1H).

By the procedures described herein the following compounds of the Tables1 to 20 can be prepared. The compounds in Table 1, line 1 can bereferred to as 1-1, 1-2, 1-3 and 1-4 (as designated by line and column,respectively). All the other specific compounds covered in these Tablescan be designated in an analogous fashion. In Tables 2-7, 9, 31-33, m is1 when R⁶ is a single substituent and m is 2 when R⁶ is twosubstituents, which can be the same or different, as indicated in thetable. The following abbreviations have been used in Tables 1-20: i=iso,n=normal, Me=methyl, Et=ethyl, Pr=propyl, Bu=butyl, Pen=pentyl,Hex=hexyl, Oct=octyl, Dec=decyl, Ph=phenyl, Pyr=pyridinyl. ##STR17##

                                      TABLE 1                                     __________________________________________________________________________    1         2       3        4                                                  __________________________________________________________________________    T = T-1, R.sup.3 = R.sup.4 = H, Z = O, R.sup.2 = F, R.sup.5 =                  1                                                                              6-CF.sub.3                                                                            5-CH.sub.2 CH.sub.3                                                                   6-OCH(CH.sub.2).sub.2                                                                  6-CO(CH.sub.2).sub.4 CH.sub.3                       2                                                                              6-Cl    7-(CH.sub.2).sub.2 CH.sub.3                                                           7-OCH(CH.sub.2).sub.2                                                                  6-COPh                                              3                                                                              6-Br    5-(CH.sub.2).sub.2 CH.sub.3                                                           6-O(CH.sub.2).sub.2 CH.sub.3                                                           6-CO(4-ClPh)                                        4                                                                              5-CF.sub.3                                                                            7-(CH.sub.2).sub.3 CH.sub.3                                                           7-O(CH.sub.2).sub.2 CH.sub.3                                                           6-CO(4-FPh)                                         5                                                                              5-Cl    5-(CH.sub.2).sub.3 CH.sub.3                                                           6-O(CH.sub.2).sub.3 CH.sub.3                                                           6-CO.sub.2 CH.sub.3                                 6                                                                              5-Br    7-(CH.sub.2).sub.4 CH.sub.3                                                           7-O(CH.sub.2).sub.3 CH.sub.3                                                           6-CO.sub.2 CH.sub.2 CH.sub.3                        7                                                                              7-CF.sub.3                                                                            7-(CH.sub.2).sub.6 CH.sub.3                                                           6-O(CH.sub.2).sub.4 CH.sub.3                                                           6-CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                8                                                                              7-Cl    7-(CH.sub.2).sub.8 CH.sub.3                                                           7-O(CH.sub.2).sub.4 CH.sub.3                                                           6-CO.sub.2 CH(CH.sub.2).sub.3                       9                                                                              7-Br    7-(CH.sub.2).sub.10 CH.sub.3                                                          6-O(CH.sub.2).sub.5 CH.sub.3                                                           6-CO.sub.2 C(CH.sub.3).sub.3                       10                                                                              8-CF.sub.3                                                                            7-(CH.sub.2).sub.12 CH.sub.3                                                          7-O(CH.sub.2).sub.5 CH.sub.3                                                           6-CO.sub.2 (CH.sub.2).sub.4 CH.sub.3               11                                                                              8-Cl    7-(CH.sub.2).sub.14 CH.sub.3                                                          6-O(CH.sub.2).sub.6 CH                                                                 6-CO.sub.2 CH.sub.2 Ph                             12                                                                              8-Br    6-CH(CH.sub.3).sub.2                                                                  7-O(CH.sub.2).sub.6 CH.sub.3                                                           6-CO.sub.2 Ph                                      13                                                                              6-CH.sub.3                                                                            7-CH(CH.sub.3).sub.2                                                                  6-O(CH.sub.2).sub.7 CH.sub.3                                                           6-4-CF.sub.3 Ph                                    14                                                                              6-CH.sub.2 CH.sub.3                                                                   5-C(CH.sub.3).sub.3                                                                   6-O(CH.sub.2).sub.8 CH.sub.3                                                           6-OCH.sub.2 OCH.sub.2 CH.sub.3                     15                                                                              6-(CH.sub.2).sub.2 CH.sub.3                                                           6-C(CH.sub.3).sub.3                                                                   6-O(CH.sub.2).sub.9 CH.sub.3                                                           6-OCH.sub.2 (4-ClPh)                               16                                                                              6-(CH.sub.2).sub.3 CH.sub.3                                                           7-C(CH.sub.3).sub.3                                                                   6-O(CH.sub.2).sub.10 CH.sub.3                                                          6-OCH.sub.2 (3-ClPh)                               17                                                                              6-(CH.sub.2).sub.4 CH.sub.3                                                           8-C(CH.sub.3).sub.3                                                                   6-O(CH.sub.2).sub.12 CH.sub.3                                                          6-OCH.sub.2 (2-ClPh)                               18                                                                              6-(CH.sub.2).sub.5 CH.sub.3                                                           6-CH.sub.2 Ph                                                                         6-O(CH.sub.2).sub.14 CH.sub.3                                                          6-OCH.sub.2 (4-MePh)                               19                                                                              6-(CH.sub.2).sub.6 CH.sub.3                                                           7-CH.sub.2 Ph                                                                         6-OPh    6-OCH.sub.2 (3-MePh)                               20                                                                              6-(CH.sub.2).sub.7 CH.sub.3                                                           6-Ph    7-OPh    6-OCH.sub.2 (2-MePh)                               21                                                                              6-(CH.sub.2).sub.8 CH.sub.3                                                           7-Ph    6-O-(2-Pyr)                                                                            6-OCH.sub.2 CH═CHCH.sub.3                      22                                                                              6-(CH.sub.2).sub.9 CH.sub.3                                                           6-cyclohexyl                                                                          6-OCH.sub.2 Ph                                                                         6-OCH.sub.2 C(Cl)═CH.sub.2                     23                                                                              6-(CH.sub.2).sub.10 CH.sub.3                                                          7-cyclohexyl                                                                          6-OCH.sub.2 -4-ClPh                                                                    6-OCH.sub.2 C(CH.sub.3)═CH.sub.2               24                                                                              6-(CH.sub.2).sub.12 CH.sub.3                                                          6-OCH.sub.3                                                                           6-OCH.sub.2 CH═CH.sub.2                                                            6-(4-Cl-Ph)                                        25                                                                              6-(CH.sub.2).sub.14 CH.sub.3                                                          7-OCH.sub.3                                                                           6-OCH.sub.2 C.tbd.CH                                                                   6-(3-Cl-Ph)                                        26                                                                              7-CH.sub.3                                                                            6-OCH.sub.2 CH.sub.3                                                                  6-OCH.sub.2 CH.sub.2 Ph                                                                6-(2-Cl-Ph)                                        27                                                                              8-CH.sub.3                                                                            7-OCH.sub.2 CH.sub.3                                                                  6-OCH.sub.2 OCH.sub.3                                                                  6-OCHF.sub.2                                       28                                                                              5-CH.sub.3                                                                            6-OCH.sub.2 CF.sub.3                                                                  6-COCH.sub.3                                                                           7-OCHF.sub.2                                       29                                                                              7-CH.sub.2 CH.sub.3                                                                   7-OCH.sub.2 CF.sub.3                                                                  6-COCH.sub.2 CH.sub.3                                                                  6-OCH(CH.sub.3)CH.sub.2 CH.sub.3                   30                                                                              8-CH.sub.2 CH.sub.3                                                                   6-OCF.sub.2 CF.sub.2 H                                                                6-CO(CH.sub.2).sub.2 CH.sub.3                                                          6-O-cyclohexyl                                     T = T-1, R.sup.3 = R.sup.4 '2 H, Z = O, R.sup.2 = Cl, R.sup.5                 31                                                                              6-CF.sub.3                                                                            5-CH.sub.2 CH.sub.3                                                                   6-OCH(CH.sub.2).sub.2                                                                  6-CO(CH.sub.2).sub.4 CH.sub.3                      32                                                                              6-Cl    7-(CH.sub.2).sub.2 CH.sub.3                                                           7-OCH(CH.sub.2).sub.2                                                                  6-COPh                                             33                                                                              6-Br    5-(CH.sub.2).sub.2 CH.sub.3                                                           6-O(CH.sub.2).sub.2 CH.sub.3                                                           6-CO(4-ClPh)                                       34                                                                              5-CF.sub.3                                                                            7-(CH.sub.2).sub.3 CH.sub.3                                                           7-O(CH.sub.2).sub.2 CH.sub.3                                                           6-CO(4-FPh)                                        35                                                                              5-Cl    5-(CH.sub.2).sub.3 CH.sub.3                                                           6-O(CH.sub.2).sub.3 CH.sub.3                                                           6-CO.sub.2 CH.sub.3                                36                                                                              5-Br    7-(CH.sub.2).sub.4 CH.sub.3                                                           7-O(CH.sub.2).sub.3 CH.sub.3                                                           6-CO.sub.2 CH.sub.2 CH.sub.3                       37                                                                              7-CF.sub.3                                                                            7-(CH.sub.2).sub.6 CH.sub.3                                                           6-O(CH.sub.2).sub.4 CH.sub.3                                                           6-CO.sub.2 (CH.sub.2).sub.2 CH.sub.3               38                                                                              7-Cl    7-(CH.sub.2).sub.8 CH.sub.3                                                           7-O(CH.sub.2).sub.4 CH.sub.3                                                           6-CO.sub.2 CH(CH.sub.2).sub.3                      39                                                                              7-Br    7-(CH.sub.2).sub.10 CH.sub.3                                                          6-O(CH.sub.2).sub.5 CH.sub.3                                                           6-CO.sub.2 C(CH.sub.3).sub.3                       40                                                                              8-CF.sub.3                                                                            7-(CH.sub.2).sub.12 CH.sub.3                                                          7-O(CH.sub.2).sub.5 CH.sub.3                                                           6-CO.sub.2 (CH.sub.2).sub.4 CH.sub.3               41                                                                              8-Cl    7-(CH.sub.2).sub.14 CH.sub.3                                                          6-O(CH.sub.2).sub.6 CH.sub.3                                                           6-CO.sub.2 CH.sub.2 Ph                             42                                                                              8-Br    6-CH(CH.sub.3).sub.2                                                                  7-O(CH.sub.2).sub.6 CH.sub.3                                                           6-CO.sub.2 Ph                                      43                                                                              6-CH.sub.3                                                                            7-CH(CH.sub.3).sub.2                                                                  6-O(CH.sub.2).sub.7 CH.sub.3                                                           6-4-CF.sub.3 -Ph                                   44                                                                              6-CH.sub.2 CH.sub.3                                                                   5-C(CH.sub.3).sub.3                                                                   6-O(CH.sub.2).sub.8 CH.sub.3                                                           6-OCH.sub.2 OCH.sub.2 CH.sub.3                     45                                                                              6-(CH.sub.2).sub.2 CH.sub.3                                                           6-C(CH.sub.3).sub.3                                                                   6-O(CH.sub.2).sub.9 CH.sub.3                                                           6-OCH.sub.2 (4-ClPh)                               46                                                                              6-(CH.sub.2).sub.3 CH.sub.3                                                           7-C(CH.sub.3).sub.3                                                                   6-O(CH.sub.2).sub.10 CH.sub.3                                                          6-OCH.sub.2 (3-ClPh)                               47                                                                              6-(CH.sub.2).sub.4 CH.sub.3                                                           8-C(CH.sub.3).sub.3                                                                   6-O(CH.sub.2).sub.12 CH.sub.3                                                          6-OCH.sub.2 (2-ClPh)                               48                                                                              6-(CH.sub.2).sub.5 CH.sub.3                                                           6-CH.sub.2 Ph                                                                         6-O(CH.sub.2).sub.14 CH.sub.3                                                          6-OCH.sub.2 (4-MePh)                               49                                                                              6-(CH.sub.2).sub.6 CH.sub.3                                                           7-CH.sub.2 Ph                                                                         6-OPh    6-OCH.sub.2 (3-MePh)                               50                                                                              6-(CH.sub.2).sub.7 CH.sub.3                                                           6-Ph    7-OPh    6-OCH.sub.2 (2-MePh)                               51                                                                              6-(CH.sub.2).sub.8 CH.sub.3                                                           7-Ph    6-O-(2-Pyr)                                                                            6-OCH.sub.2 CH═CHCH.sub.3                      52                                                                              6-(CH.sub.2).sub.9 CH.sub.3                                                           6-cyclohexyl                                                                          6-OCH.sub.2 Ph                                                                         6-OCH.sub.2 C(Cl)═CH.sub.2                     53                                                                              6-(CH.sub.2).sub.10 CH.sub.3                                                          7-cyclohexyl                                                                          6-OCH.sub.2 -4-ClPh                                                                    6-OCH.sub.2 C(CH.sub.3)═CH.sub.2               54                                                                              6-(CH.sub.2).sub.12 CH.sub.3                                                          6-OCH.sub.3                                                                           6-OCH.sub.2 CH═CH.sub.2                                                            6-(4-Cl-Ph)                                        55                                                                              6-(CH.sub.2).sub.14 CH.sub.3                                                          7-OCH.sub.3                                                                           6-OCH.sub.2 C═CH                                                                   6-(3-Cl-Ph)                                        56                                                                              7-CH.sub.3                                                                            6-OCH.sub.2 CH.sub.3                                                                  6-OCH.sub.2 CH.sub.2 Ph                                                                6-(2-Cl-Ph)                                        57                                                                              8-CH.sub.3                                                                            7-OCH.sub.2 CH.sub.3                                                                  6-OCH.sub.2 OCH.sub.3                                                                  6-OCHF.sub.2                                       58                                                                              5-CH.sub.3                                                                            6-OCH.sub.2 CF.sub.3                                                                  6-COCH.sub.3                                                                           7-OCHF.sub.2                                       59                                                                              7-CH.sub.2 CH.sub.3                                                                   7-OCH.sub.2 CF.sub.3                                                                  6-COCH.sub.2 CH.sub.3                                                                  6-OCH(CH.sub.3)CH.sub.2 CH.sub.3                   60                                                                              8-CH.sub.2 CH.sub.3                                                                   6-OCF.sub.2 CF.sub.2 H                                                                6-CO(CH.sub.2).sub.2 CH.sub.3                                                          6-O-cyclohexyl                                     T = T-1, R.sup.3 = 3-Cl, R.sup.4 = H, Z = O, R.sup.2 = F, R.sup.5 =           61                                                                              6-H     5-CF.sub.3                                                                            6-CF.sub.3                                                                             7-CF.sub.3                                         62                                                                              5-Cl    6-Cl    7-Cl     5-CH.sub.3                                         63                                                                              6-CH.sub.3                                                                            7-CH.sub.3                                                                            5-C(CH.sub.3).sub.3                                                                    6-C(CH.sub.3).sub.3                                64                                                                              7-C(CH.sub.3).sub.3                                                                   6-(CH.sub.2).sub.2 CH.sub.3                                                           6-(CH.sub.2).sub.3 CH.sub.3                                                            6-(CH.sub.2).sub.4 CH.sub.3                        65                                                                              6-(CH.sub.2).sub.6 CH.sub.3                                                           6-(CH.sub.2).sub.8 CH.sub.3                                                           6-OCH.sub.3                                                                            6-OCH.sub.2 CH.sub.3                               66                                                                              6-OCH(CH.sub.3).sub.2                                                                 6-O(CH.sub.2).sub.2 CH.sub.3                                                          6-O(CH.sub.2).sub.3 CH.sub.3                                                           6-O(CH.sub.2).sub.4 CH.sub.3                       67                                                                              6-O(CH.sub.2).sub.6 CH.sub.3                                                          6-O(CH.sub.2).sub.8 CH.sub.3                                                          6-OCF.sub.2 CF.sub.2 H                                                                 6-OCH.sub.2 CF.sub.3                               68                                                                              6-OCH.sub.2 OCH.sub.3                                                                 6-OPh   6-OCH.sub.2 Ph                                                                         6-CO.sub.2 CH.sub.3                                69                                                                              6-COCH.sub.3                                                                          6-Ph    7-Ph     7-OPh                                              70                                                                              6-COPh  6-COCF.sub.3                                                                          6-O(CH.sub.2).sub.2 Ph                                                                 6-CH.sub.2 Ph                                      T = T-1, R.sup.3 = R.sup.4 = H, Z = S, R.sup.2 = F, R.sup.5 =                 71                                                                              6-H     5-CF.sub.3                                                                            6-CF.sub.3                                                                             7-CF.sub.3                                         72                                                                              5-Cl    6-Cl    7-Cl     5-CH.sub.3                                         73                                                                              6-CH.sub.3                                                                            7-CH.sub.3                                                                            5-C(CH.sub.3).sub.3                                                                    6-C(CH.sub.3).sub.3                                74                                                                              7-C(CH.sub.3).sub.3                                                                   6-(CH.sub.2).sub.2 CH.sub.3                                                           6-(CH.sub.2).sub.3 CH.sub.3                                                            6-(CH.sub.2).sub.4 CH.sub.3                        75                                                                              6-(CH.sub.2).sub.6 CH.sub.3                                                           6-(CH.sub.2).sub.8 CH.sub.3                                                           6-OCH.sub.3                                                                            6-OCH.sub.2 CH.sub.3                               76                                                                              6-OCH(CH.sub.3).sub.2                                                                 6-O(CH.sub.2).sub.2 CH.sub.3                                                          6-O(CH.sub.2).sub.3 CH.sub.3                                                           6-O(CH.sub.2).sub.4 CH.sub.3                       77                                                                              6-O(CH.sub.2).sub.6 CH.sub.3                                                          6-O(CH.sub.2).sub.8 CH.sub.3                                                          6-OCF.sub.2 CF.sub.2 H                                                                 6-OCH.sub.2 CF.sub.3                               78                                                                              6-OCH.sub.2 OCH.sub.3                                                                 6-OPh   6-OCH.sub.2 Ph                                                                         6-CO.sub.2 CH.sub.3                                79                                                                              6-COCH.sub.3                                                                          6-Ph    7-Ph     7-OPh                                              80                                                                              6-COPh  6-COCF.sub.3                                                                          6-O(CH.sub.2).sub.2 Ph                                                                 6-CH.sub.2 Ph                                      __________________________________________________________________________

                  TABLE 2                                                         ______________________________________                                        T = T-2, R.sup.3 = R.sup.4 = H, m = 1 or 2, R.sup.6 =                         1           2          3          4                                           ______________________________________                                        81    H         5-Me       5-Et     5-n-Pr                                    82    5-n-Bu    5-n-Hex    6-Me     6-Et                                      83    6-n-Bu    7-Me       7-Et     5,5-diMe                                  84    5,5-diEt  5-Me,5-Et  6,6-diMe 6,6-diEt                                  85    7,7-diMe  5-Me,6-Me  5-Me,6-Me                                                                              5-Me,7-Me                                 ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                        T = T-3, R.sup.3 = R.sup.4 = H, m = 1 or 2, R.sup.6 =                         1            2          3         4                                           ______________________________________                                        86     H         5-Me       5-Et    5-n-Pr                                    87     5-n-Bu    6-Me       7-Me    8-Me                                      88     5,5-diMe  6,6-diMe   7,7-diMe                                                                              8,8-diMe                                  89     6-Et      6-n-Bu     7-Et    7-n-Bu                                    90     8-Et      8-n-Bu     5-n-Hex 6-n-Hex                                   ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                        T = T-4, R.sup.3 = R.sup.4 = H, m = 1 or 2, R.sup.6 =                         1            2          3         4                                           ______________________________________                                        91     H         5-Me       5-Et    5-n-Pr                                    92     6-Me      7-Me       8-Me    9-Me                                      93     6,6-diMe  7,7-diMe   8,8-diMe                                                                              9,9-diMe                                  94     6-Et      7-Et       8-Et    9-Et                                      95     5-n-Bu    5-n-Hex    9-n-Bu  9-n-Hex                                   ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                        T = T-5, R.sup.3 = R.sup.4 = H, m = 1 or 2, R.sup.6 =                         1          2           3          4                                           ______________________________________                                        96   H         6-Me        6-Et     6-n-Pr                                    97   6-n-Bu    6-n-Pen     6-n-Oct  6-n-Dec                                   98   6-i-Pr    6-t-Bu      6,6-diF  6,6-diMe                                  99   6-Ph      6-(3-Cl-Ph) 6-(2-Cl-Ph)                                                                            6-Me,6-Et                                 100  6-Me,6-Ph 6-Me,6-n-Bu 6-Me,6-n-Hex                                                                           6,6-diEt                                  ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                        T = T-6, R.sup.3 = R.sup.4 = H, m = 1 or 2, R.sup.6 =                         1            2          3         4                                           ______________________________________                                        101    H         6-Me       6-Et    6-n-Pr                                    102    7-Me      7-Et       7-n-Pr  6,6-diMe                                  103    6-n-Bu    6-n-Hex    6,6-diEt                                                                              7,7-diMe                                  104    7,7-diEt  6-Ph       7-Ph    6-Me,6-Et                                 ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                        T = T-7, R.sup.3 = R.sup.4 = H, m = 1 or 2, R.sup.6 =                         1            2          3         4                                           ______________________________________                                        105    H         6-Me       7-Me    8-Me                                      106    6-Et      7-Et       8-Et    6,6-diMe                                  107    7,7-diMe  6,6-diEt   6-Ph    7-Ph                                      108    8-Ph      6-Me,6-Et  6-Me,6-Ph                                                                             7-Me,7-Ph                                 ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                        1            2          3         4                                           ______________________________________                                        T = T-8, R.sup.3 = R.sup.4 = H, G = S, R.sup.5 =                              109    H         6-Bu       7-Bu    6-CF.sub.3                                110    7-CF.sub.3                                                                              6-Me       7-Me    6-Et                                      111    7-Et      6-n-Pr     6-i-Pr  6-n-Bu                                    112    6-n-Hex   6-n-Oct    6-OMe   6-OEt                                     113    6-O-n-Pr  6-O-i-Pr   6-O-n-Bu                                                                              6-O-n-Hex                                 114    6-O-n-Oct 6-COCH.sub.3                                                                             6-CO.sub.2 Et                                                                         6-COPh                                    T = T-8, R.sup.3 = R.sup.4 = H, G = S, R.sup.5 =                              115    H         6-Bu       7-Bu    6-CF.sub.3                                116    7-CF.sub.3                                                                              6-Me       7-Me    6-Et                                      117    7-Et      6-n-Pr     6-i-Pr  6-n-Bu                                    118    6-n-Hex   6-n-Oct    6-OMe   6-OEt                                     119    6-O-n-Pr  6-O-i-Pr   6-O-n-Bu                                                                              6-O-n-Hex                                 120    6-O-n-Oct 6-COCH.sub.3                                                                             6-CO.sub.2 Et                                                                         6-COPh                                    ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                        1            2          3         4                                           ______________________________________                                        T = T-9, R.sup.3 = R.sup.4 = H, G = O, R.sup.2 = F, m = 1 or 2, R.sup.6       121    6-H       6-Me       6-Et    6-n-Pr                                    122    6-n-Bu    6-n-Hex    6-n-Oct 6,6-diMe                                  123    6,6-diEt  6-Me,6-Et  6-Me,6-Ph                                                                             6-Me,6-n-Bu                               124    7-Me      7-Et       7-n-Pr  7-n-Bu                                    T = T-9, R.sup.3 = R.sup.4 = H, G = O, R.sup.2 = Cl, m = 1 or 2, R.sup.6      =                                                                             125    6-H       6-Me       6-Et    6-n-Pr                                    126    6-n-Bu    6-n-Hex    6-n-Oct 6,6-diMe                                  127    6,6-diEt  6-Me,6-Et  6-Me,6-Ph                                                                             6-Me,6-n-Bu                               128    7-Me      7-Et       7-n-Pr  7-n-Bu                                    T = T-9, R.sup.3 = R.sup.4 = H, G = S, R.sup.2 = F, m = 1 or 2, R.sup.6       =                                                                             129    6-H       6-Me       6-Et    6-n-Pr                                    130    6-n-Bu    6-n-Hex    6-n-Oct 6,6-diMe                                  131    6,6-diEt  6-Me,6-Et  6-Me,6-Ph                                                                             6-Me,6-n-Bu                               132    7-Me      7-Et       7-n-Pr  7-n-Bu                                    T = T-9, R.sup.3 = R.sup.4 = H, G = S, R.sup.2 = Cl, m = 1 or 2, R.sup.6      =                                                                             133    6-H       6-Me       6-Et    6-n-Pr                                    134    6-n-Bu    6-n-Hex    6-n-Oct 6,6-diMe                                  135    6,6-diEt  6-Me,6-Et  6-Me,6-Ph                                                                             6-Me,6-n-Bu                               136    7-Me      7-Et       7-n-Pr  7-n-Bu                                    ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                        T = T-10, R.sup.3 = R.sup.4 = H, R .sup.5 =                                   1             2         3         4                                           ______________________________________                                        137   H           7-Bu      8-Bu    7-Cl                                      138   8-Cl        6-Cl      5-Cl    7-CF.sub.3                                139   8-CF.sub.3  8-Me      7-Me    8-Et                                      140   7-Et        8-n-Pr    8-n-Bu  8-n-Hex                                   141   8-n-Oct     8-i-Pr    8-OMe   8-OEt                                     142   8-OCH.sub.2 CF.sub.3                                                                      8-O-n-Bu  8-CO.sub.2 Et                                                                         8-COCH.sub.3                              ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                        1            2          3         4                                           ______________________________________                                        T = T-11, R.sup.5 = H, G = O, R.sup.3 =                                       143    H         5-Cl       6-Cl    7-Cl                                      144    4-Cl      5-CF.sub.3 6-CF.sub.3                                                                            5-Me                                      145    5-Et      5-n-Pr     5-n-Bu  5-n-Hex                                   146    5-n-Oct   6-Me       6-Et    6-n-Bu                                    147    5-OMe     5-OEt      5-O-i-Pr                                                                              5-O-n-Pr                                  148    5-O-n-Pr  5-O-n-Hex  5-O-n-Oct                                                                             6-OMe                                     149    6-OEt     6-O-i-Pr   5-CO.sub.2 Et                                                                         5-COCH.sub.3                              150    5-COPh    6-CO.sub.2 Et                                                                            6-COCH.sub.3                                                                          6-COPh                                    T = T-11, R.sup.5 = H, G = S, R.sup.3 =                                       151    H         5-Cl       6-Cl    7-Cl                                      152    4-Cl      5-CF.sub.3 6-CF.sub.3                                                                            5-Me                                      153    5-Et      5-n-Pr     5-n-Bu  5-n-Hex                                   154    5-n-Oct   6-Me       6-Et    6-n-Bu                                    155    5-OMe     5-OEt      5-O-i-Pr                                                                              5-O-n-Pr                                  156    5-O-n-Pr  5-O-n-Hex  5-O-n-Oct                                                                             6-OMe                                     157    6-OEt     6-O-i-Pr   5-CO.sub.2 Et                                                                         5-COCH.sub.3                              158    5-COPh    6-CO.sub.2 Et                                                                            6-COCH.sub.3                                                                          6-COPh                                    ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                        1            2          3         4                                           ______________________________________                                        T = T-12, R.sup.5 = H, G = O, R.sup.3 =                                       159    H         5-Cl       6-Cl    7-Cl                                      160    4-Cl      5-CF.sub.3 6-CF.sub.3                                                                            5-Me                                      161    5-Et      5-n-Pr     5-n-Bu  5-n-Hex                                   162    5-n-Oct   6-Me       6-Et    6-n-Bu                                    163    5-OMe     5-OEt      5-O-i-Pr                                                                              5-O-n-Pr                                  164    5-O-n-Pr  5-O-n-Hex  5-O-n-Oct                                                                             6-OMe                                     165    6-OEt     6-O-i-Pr   5-CO.sub.2 Et                                                                         5-COCH.sub.3                              166    5-COPh    6-CO.sub.2 Et                                                                            6-COCH.sub.3                                                                          6-COPh                                    T = T-12, R.sup.5 = H, G = S, R.sup.3 =                                       167    H         5-Cl       6-Cl    7-Cl                                      168    4-Cl      5-CF.sub.3 6-CF.sub.3                                                                            5-Me                                      169    5-Et      5-n-Pr     5-n-Bu  5-n-Hex                                   170    5-n-Oct   6-Me       6-Et    6-n-Bu                                    171    5-OMe     5-OEt      5-O-i-Pr                                                                              5-O-n-Pr                                  172    5-O-n-Pr  5-O-n-Hex  5-O-n-Oct                                                                             6-OMe                                     173    6-OEt     6-O-i-Pr   5-CO.sub.2 Et                                                                         5-COCH.sub.3                              174    5-COPh    6-CO.sub.2 Et                                                                            6-COCH.sub.3                                                                          6-COPh                                    ______________________________________                                    

                                      TABLE 13                                    __________________________________________________________________________    1          2        3             4                                           __________________________________________________________________________    T = T-13, R.sup.2 = F, Z = O, R.sup.3 =                                       175                                                                              5-CF.sub.3                                                                            5-C(CH.sub.3).sub.3                                                                    5-CH.sub.2 (4-Cl-Ph)                                                                        5-(4-Cl-Ph)                                 176                                                                              4-CF.sub.3                                                                            4-C(CH.sub.3).sub.3                                                                    4-CH.sub.2 (4-Cl-Ph)                                                                        4-(4-Cl-Ph)                                 177                                                                              5-Cl    5-CH(CH.sub.3).sub.2                                                                   5-CH.sub.2 (4-Br-Ph)                                                                        5-(4-Br-Ph)                                 178                                                                              4-Cl    4-CH(CH.sub.3).sub.2                                                                   5-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 5-(4-CF.sub.3 -Ph)                          179                                                                              5-Br    5-cyclohexyl                                                                           4-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 4-(4-CF.sub.3 -Ph)                          180                                                                              4-Br    4-cyclohexyl                                                                           5-CH.sub.2 (3-Br-Ph)                                                                        5-(3-Br-Ph)                                 181                                                                              5-CH.sub.3                                                                            5-O(CH.sub.2).sub.5 CH.sub.3                                                           5-CH.sub.2 (3-CF.sub.3 -Ph)                                                                 5-(3-CF.sub.3 -Ph)                          182                                                                              4-CH.sub.3                                                                            4-O(CH.sub.2).sub.5 CH.sub.3                                                           5-CH.sub.2 (2-Cl-Ph)                                                                        5-(2-Cl-Ph)                                 183                                                                              5-CH.sub.2 CH.sub.3                                                                   5-O(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 (4-OMe-Ph)                                                                       5-(4-OMe-Ph)                                184                                                                              4-CH.sub.2 CH.sub.3                                                                   4-O(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 (2,4-di-Cl-Ph)                                                                   5-(2,4-di-Cl-Ph)                            185                                                                              5-(CH.sub.2).sub.2 CH.sub.3                                                           5-O(CH.sub.2).sub.9 CH.sub.3                                                           4-CH.sub.2 (2,4-di-Cl-Ph)                                                                   4-(2,4-di-Cl-Ph)                            186                                                                              4-(CH.sub.2).sub.2 CH.sub.3                                                           4-O(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 (2,5-di-Cl-Ph)                                                                   5-(2,5-di-Cl-Ph)                            187                                                                              5-(CH.sub.2).sub.3 CH.sub.3                                                           5-O(CH.sub.2).sub.11 CH.sub.3                                                          5-CH.sub.2 (2,3-di-Cl-Ph)                                                                   5-(2,3-di-Cl-Ph)                            188                                                                              4-(CH.sub.2).sub.3 CH.sub.3                                                           4-O(CH.sub.2).sub.11 CH.sub.3                                                          5-CH.sub.2 (2,6-di-Cl-Ph)                                                                   5-(2,6-di-Cl-Ph)                            189                                                                              5-(CH.sub.2).sub.4 CH.sub.3                                                           5-OPh    5-CH.sub.2 (3,4-di-Cl-Ph)                                                                   5-(3,4-di-Cl-Ph)                            190                                                                              4-(CH.sub.2).sub.4 CH.sub.3                                                           4-OPh    5-CH.sub.2 (3,5-di-Cl-Ph)                                                                   5-(3,5-di-Cl-Ph)                            191                                                                              5-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                         5-CH.sub.2 (3-Cl,4-F-Ph)                                                                    5-(3-Cl,4-F-Ph)                             192                                                                              4-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                         5-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            5-(2-Cl,4-CF.sub.3 -Ph)                     193                                                                              5-(CH.sub.2).sub.6 CH.sub.3                                                           5-Pyr    4-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            4-(2-Cl,4-CF.sub.3 -Ph)                     194                                                                              4-(CH.sub.2).sub.6 CH.sub.3                                                           4-Pyr    5-CH.sub.2 (2-F,5-OMe-Ph)                                                                   5-(2-F,5-OMe-Ph)                            T = T-13, R.sup.2 = F, Z = O, R.sup.3 =                                       195                                                                              5-(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 Pyr                                                                         5-CH.sub.2 (2-F,5-Me-Ph)                                                                    5-(2-F,5-Me-Ph)                             196                                                                              4-(CH.sub.2).sub.7 CH.sub.3                                                           4-CH.sub.2 Pyr                                                                         5-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                5-(2,4,5-tri-Cl-Ph)                         197                                                                              5-(CH.sub.2).sub.8 CH.sub.3                                                           5-O-Pyr  4-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                4-(2,4,5-tri-Cl-Ph)                         198                                                                              4-(CH.sub.2).sub.8 CH.sub.3                                                           4-O-Pyr  5-CH.sub.2 (2,4,5-tri-F-Ph)                                                                 5-(2,4,5-tri-F-Ph)                          199                                                                              5-(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 Ph                                                                          5-CH.sub.2 (2,4-di-Cl,4-CF.sub.3 -Ph)                                                       5-(2,4-di-Cl,5-CF.sub.3 -Ph)                200                                                                              4-(CH.sub.2).sub.9 CH.sub.3                                                           4-CH.sub.2 Ph                                                                          4-CH.sub.2 (2,4-di-Cl,5-CF.sub.3 -Ph)                                                       4-(2,4-di-Cl,5-CF.sub.3 -Ph)                201                                                                              5-(CH.sub.2).sub.11 CH.sub.3                                                          5-Ph     5-CH.sub.2 (2-Cl,5-CO.sub.2 Me-Ph)                                                          5-(2-Cl,5-CO.sub.2 Me-Ph)                   202                                                                              4-(CH.sub.2).sub.11 CH.sub.3                                                          4-Ph     4-CH.sub.2 (2-Cl,5-CO.sub.2 Me-Ph)                                                          4-(2-Cl,5-CO.sub.2 Me-Ph)                   203                                                                              5-(CH.sub.2).sub.13 CH.sub.3                                                          5-O-cyclohexyl                                                                         5-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             5-(2,4-di-Cl,5-OMe-Ph)                      204                                                                              4-(CH.sub.2).sub.13 CH.sub.3                                                          4-O-cyclohexyl                                                                         4-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             4-(2,4-di-Cl,5-OMe-Ph)                      T = T-13, R.sup.2 = Cl, Z = O, R.sup.3 =                                      205                                                                              5-CF.sub.3                                                                            5-C(CH.sub.3).sub.3                                                                    5-CH.sub.2 (4-Cl-Ph)                                                                        5-(4-Cl-Ph)                                 206                                                                              4-CF.sub.3                                                                            4-C(CH.sub.3).sub.2                                                                    5-CH.sub.2 (4-Br-Ph)                                                                        5-(4-Br-Ph)                                 207                                                                              4-Cl    4-CH(CH.sub.3).sub.2                                                                   5-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 5-(4-CF.sub.3 -Ph)                          208                                                                              5-Br    5-cyclohexyl                                                                           4-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 4-(4-CF.sub.3 -Ph)                          209                                                                              4-Br    4-cyclohexyl                                                                           5-CH.sub.2 (3-Br-Ph)                                                                        5-(3-Br-Ph)                                 210                                                                              5-CH.sub.3                                                                            5-O(CH.sub.2).sub.5 CH.sub.3                                                           5-CH.sub.2 (3-CF.sub.3 -Ph)                                                                 5-(3-CF.sub.3 -Ph)                          211                                                                              4-CH.sub.3                                                                            4-O(CH.sub.2).sub.5 CH.sub.3                                                           5-CH.sub.2 (2-Cl-Ph)                                                                        5-(2-Cl-Ph)                                 212                                                                              5-CH.sub.2 CH.sub.3                                                                   5-O(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 (4-OMe-Ph)                                                                       5-(4-OMe-Ph)                                213                                                                              4-CH.sub.2 CH.sub.3                                                                   4-O(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 (2,4-di-Cl-Ph)                                                                   5-(2,4-di-Cl-Ph)                            214                                                                              5-(CH.sub.2).sub.2 CH.sub.3                                                           5-O(CH.sub.2).sub.9 CH.sub.3                                                           4-CH.sub.2 (2,4-di-Cl-Ph)                                                                   4-(2,4-di-Cl-Ph)                            215                                                                              4-(CH.sub.2).sub.2 CH.sub.3                                                           4-O(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 (2,5-di-Cl-Ph)                                                                   5-(2,5-di-Cl-Ph)                            216                                                                              5-(CH.sub.2).sub.3 CH.sub.3                                                           5-O(CH.sub.2).sub.11 CH.sub.3                                                          5-CH.sub.2 (2,3-di-Cl-Ph)                                                                   5-(2,3-di-Cl-Ph)                            217                                                                              4-(CH.sub.2).sub.3 CH.sub.3                                                           4-O(CH.sub.2).sub.11 CH.sub.3                                                          5-CH.sub.2 (2,6-di-Cl-Ph)                                                                   5-(2,6-di-Cl-Ph)                            218                                                                              5-(CH.sub.2).sub.4 CH.sub.3                                                           5-OPh    5-CH.sub.2 (3,4-di-Cl-Ph)                                                                   5-(3,4-di-Cl-Ph)                            219                                                                              4-(CH.sub.2).sub.4 CH.sub.3                                                           4-OPh    5-CH.sub.2 (3,5-di-Cl-Ph)                                                                   5-(3,5-di-Cl-Ph)                            220                                                                              5-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                         5-CH.sub.2 (3-Cl,4-F-Ph)                                                                    5-(3-Cl,4-F-Ph)                             T = T-13, R.sup.2 = Cl, Z = O, R.sup.3 =                                      221                                                                              4-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                         5-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            5-(2-Cl,4-CF.sub.3 -Ph)                     222                                                                              5-(CH.sub.2).sub.6 CH.sub.3                                                           5-Pyr    4-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            4-(2-Cl,4-CF.sub.3 -Ph)                     223                                                                              4-(CH.sub.2).sub.6 CH.sub.3                                                           4-Pyr    5-CH.sub.2 (2-F,5-OMe-Ph)                                                                   5-(2-F,5-OMe-Ph)                            224                                                                              5-(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 Pyr                                                                         5-CH.sub.2 (2-F,5-Me-Ph)                                                                    5-(2-F,5-Me-Ph)                             225                                                                              4-(CH.sub.2).sub.7 CH.sub.3                                                           4-CH.sub.2 Pyr                                                                         5-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                5-(2,4,5-tri-Cl-Ph)                         226                                                                              5-(CH.sub.2).sub.8 CH.sub.3                                                           5-O-Pyr  4-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                4-(2,4,5-tri-Cl-Ph)                         227                                                                              4-(CH.sub.2).sub.8 CH.sub.3                                                           4-O-Pyr  5-CH.sub.2 (2,4,5-tri-F-Ph)                                                                 5-(2,4,5-tri-F-Ph)                          228                                                                              5-(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 Ph                                                                          5-CH.sub.2 (2,4-di-Cl,5-CF.sub.3 -Ph)                                                       5-(2,4-di-Cl,5-CF.sub.3 -Ph)                229                                                                              4-(CH.sub.2).sub.9 CH.sub.3                                                           4-CH.sub.2 Ph                                                                          4-CH.sub.2 (2,4-di-Cl,5-CF.sub.3 -Ph)                                                       4-(2,4-di-Cl,5-CF.sub.3 -Ph)                230                                                                              5-(CH.sub.2).sub.11 CH.sub.3                                                          5-Ph     5-CH.sub.2 (2-Cl,5-CO.sub.2 Me-Ph)                                                          5-(2-Cl,5-CO.sub.2 Me-Ph)                   231                                                                              4-(CH.sub.2).sub.11 CH.sub.3                                                          4-Ph     4-CH.sub.2 (2-Cl,5-CO.sub.2 Me-Ph)                                                          4-(2-Cl,5-CO.sub.2 Me-Ph)                   232                                                                              5-(CH.sub.2).sub.13 CH.sub.3                                                          5-O-cyclohexyl                                                                         5-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             5-(2,4-di-Cl,5-OMe-Ph)                      233                                                                              4-(CH.sub.2).sub.13 CH.sub.3                                                          4-O-cyclohexyl                                                                         4-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             4-(2,4-di-Cl,5-OMe-Ph)                      T = T-13, R.sup.2 = F, Z = O, R.sup.3 =                                       234                                                                              5-CF.sub.3                                                                            5-C(CH.sub.3).sub.3                                                                    5-CH.sub.2 (4-Cl-Ph)                                                                        5-(4-Cl-Ph)                                 235                                                                              5-Br    5-O(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 5-(4-CF.sub.3 -Ph)                          236                                                                              5-(CH.sub.2).sub.4 CH.sub.3                                                           5-OPh    5-CH.sub.2 (3-CF.sub.3 -Ph)                                                                 5-(3-CF.sub.3 -Ph)                          237                                                                              5-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                         5-CH.sub.2 (2,4-di-Cl-Ph)                                                                   5-(2,4-di-Cl-Ph)                            238                                                                              5-(CH.sub.2).sub.6 CH.sub.3                                                           5-Pyr    5-CH.sub.2 (2,5-di-Cl-Ph)                                                                   5-(2,5-di-Cl-Ph)                            239                                                                              5-(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 Pyr                                                                         5-CH.sub.2 (3-Cl,4-F-Ph)                                                                    5-(3-Cl,4-F-Ph)                             240                                                                              5-(CH.sub.2).sub.8 CH.sub.3                                                           5-O-Pyr  5-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            5-(2-Cl,4-CF.sub.3 -Ph)                     241                                                                              5-(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 Ph                                                                          5-CH.sub.2 (2-F,5-OMe-Ph)                                                                   5-(2-F,5-OMe-Ph)                            242                                                                              5-CH(CH.sub.3).sub.2                                                                  5-Ph     5-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                5-(2,4,5-tri-Cl-Ph)                         243                                                                              5-cyclohexyl                                                                          5-O-cyclohexyl                                                                         5-CH.sub.2 (2,4-di-Cl,5-CF.sub.3 -Ph)                                                       5-(2,4-di-Cl,5-CF.sub.3 -Ph)                244                                                                              5-O(CH.sub.2).sub.7 CH.sub.3                                                          5-O(CH.sub.2).sub.11 CH.sub.3                                                          5-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             5-(2,4-di-Cl,5-OMe-Ph)                      __________________________________________________________________________

                                      TABLE 14                                    __________________________________________________________________________    T = T-14, R.sup.3 =                                                           1          2       3             4                                            __________________________________________________________________________    245                                                                              5-CF.sub.3                                                                            5-C--(CH.sub.3).sub.3                                                                 5-CH.sub.2 (4,-Cl-Ph)                                                                       5-(4-Cl-Ph)                                  246                                                                              5-Br    5-O(CH.sub.2).sub.9 CH.sub.3                                                          5-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 5-(4-CF.sub.3 -Ph)                           247                                                                              5-(CH.sub.2).sub.4 CH.sub.3                                                           5-OPh   5-CH.sub.2 (8-CF.sub.3 -Ph)                                                                 5-(3-CF.sub.3 Ph)                            248                                                                              5-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                        5-CH.sub.2 (2,4-di-Cl-Ph)                                                                   5-(2,4-di-Cl-Ph)                             249                                                                              5-(CH.sub.2).sub.6 CH.sub.3                                                           5-Pyr   5-CH.sub.2 (2,5-di-Cl-Ph)                                                                   5-(2,5-di-Cl-Ph)                             250                                                                              5-(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 Pyr                                                                        5-CH.sub.2 (3-Cl,4-F-Ph)                                                                    5-(3-Cl,4-F-Ph)                              251                                                                              5-(CH.sub.2).sub.8 CH.sub.3                                                           5-O-Pyr 5-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            5-(2-Cl,4-CF.sub.3 -Ph)                      252                                                                              5-(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 Ph                                                                         5-CH.sub.2 (2-F,5-OMe-Ph)                                                                   5-(2-F,5-OMe-Ph)                             253                                                                              5-CH(CH.sub.3).sub.2                                                                  5-Ph    5-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                5-(2,4,5-tri-Cl-Ph)                          254                                                                              5-cyclohexyl                                                                          5-O-cyclohexyl                                                                        5-CH.sub.2 (2,4-di-Cl,5-CF.sub.3 -Ph)                                                       5-(2,4-di-Cl,5-CF.sub.3 -Ph)                 255                                                                              5-O(CH.sub.2).sub.7 CH.sub.3                                                          5-O(CH.sub.2).sub.11 CH.sub.3                                                         5-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             5-(2,4-di-Cl,5-OMe-Ph)                       __________________________________________________________________________

                                      TABLE 15                                    __________________________________________________________________________    T = T-15, R.sup.3 =                                                           1          2       3             4                                            __________________________________________________________________________    256                                                                              5-CF.sub.3                                                                            5-C--(CH.sub.3).sub.3                                                                 5-CH.sub.2 (4,-Cl-Ph)                                                                       5-(4-Cl-Ph)                                  257                                                                              5-Br    5-O(CH.sub.2).sub.9 CH.sub.3                                                          5-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 5-(4-CF.sub.3 -Ph)                           258                                                                              5-(CH.sub.2).sub.4 CH.sub.3                                                           5-OPh   5-CH.sub.2 (3-CF.sub.3 -Ph)                                                                 5-(3-CF.sub.3 -Ph)                           259                                                                              5-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                        5-CH.sub.2 (2,4-di-Cl-Ph)                                                                   5-(2,4-di-Cl-Ph)                             260                                                                              5-(CH.sub.2).sub.6 CH.sub.3                                                           5-Pyr   5-CH.sub.2 (2,5-di-Cl-Ph)                                                                   5-(2,5-di-Cl-Ph)                             261                                                                              5-(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 Pyr                                                                        5-CH.sub.2 (3-Cl,4-F-Ph)                                                                    5-(3-Cl,4-F-Ph)                              262                                                                              5-(CH.sub.2).sub.8 CH.sub.3                                                           5-O-Pyr 5-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            5-(2-Cl,4-CF.sub.3 -Ph)                      263                                                                              5-(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 Ph                                                                         5-CH.sub.2 (2-F,5-OMe-Ph)                                                                   5-(2-F,5-OMe-Ph)                             264                                                                              5-CH(CH.sub.3).sub.2                                                                  5-Ph    5-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                5-(2,4,5-tri-Cl-Ph)                          265                                                                              5-cyclohexyl                                                                          5-O-cyclohexyl                                                                        5-CH-(2,4-di-Cl,5-CF.sub.3 -Ph)                                                             5-(2,4-di-Cl,5-CF.sub.3 -Ph)                 266                                                                              5-O(CH.sub.2).sub.7 CH.sub.3                                                          5-O(CH.sub.2).sub.11 CH.sub.3                                                         5-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             5-(2,4-di-Cl,5-OMe-Ph)                       __________________________________________________________________________

                                      TABLE 16                                    __________________________________________________________________________    T = T-16, R.sup.3 =                                                           1          2       3             4                                            __________________________________________________________________________    267                                                                              5-CF.sub.3                                                                            5-C--(CH.sub.3).sub.3                                                                 5-CH.sub.2 (4,-Cl-Ph)                                                                       5-(4-Cl-Ph)                                  268                                                                              5-Br    5-O(CH.sub.2).sub.9 CH.sub.3                                                          5-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 5-(4-CF.sub.3 -Ph)                           269                                                                              5-(CH.sub.2).sub.4 CH.sub.3                                                           5-OPh   5-CH.sub.2 (3-CF.sub.3 -Ph)                                                                 5-(3-CF.sub.3 -Ph)                           270                                                                              5-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                        5-CH.sub.2 (2,4-di-Cl-Ph)                                                                   5-(2,4-di-Cl-Ph)                             271                                                                              5-(CH.sub.2).sub.6 CH.sub.3                                                           5-Pyr   5-CH.sub.2 (2,5-di-Cl-Ph)                                                                   5-(2,5-di-Cl-Ph)                             272                                                                              5-(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 Pyr                                                                        5-CH.sub.2 (3-Cl,4-F-Ph)                                                                    5-(3-Cl,4-F-Ph)                              273                                                                              5-(CH.sub.2).sub.8 CH.sub.3                                                           5-O-Pyr 5-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            5-(2-Cl,4-CF.sub.3 -Ph)                      274                                                                              5-(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 Ph                                                                         5-CH.sub.2 (2-F,5-OMe-Ph)                                                                   5-(2-F,5-OMe-Ph)                             275                                                                              5-CH(CH.sub.3).sub.2                                                                  5-Ph    5-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                5-(2,4,5-tri-Cl-Ph)                          276                                                                              5-cyclohexyl                                                                          5-O-cyclohexyl                                                                        5-CH.sub.2 (2,4-di-Cl,5-CF.sub.3 -Ph)                                                       5-(2,4-di-Cl,5-CF.sub.3 -Ph)                 277                                                                              5-O(CH.sub.2).sub.7 CH.sub.3                                                          5-O(CH.sub.2).sub.11 CH.sub.3                                                         5-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             5-(2,4-di-Cl,5-OMe-Ph)                       __________________________________________________________________________

                                      TABLE 17                                    __________________________________________________________________________    T = T-17, R.sup.3 =                                                           1          2       3             4                                            __________________________________________________________________________    278                                                                              5-CF.sub.3                                                                            5-C--(CH.sub.3).sub.3                                                                 5-CH.sub.2 (4,-Cl-Ph)                                                                       5-(4-Cl-Ph)                                  279                                                                              5-Br    5-O(CH.sub.2).sub.9 CH.sub.3                                                          5-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 5-(4-CF.sub.3 -Ph)                           280                                                                              5-(CH.sub.2).sub.4 CH.sub.3                                                           5-OPh   5-CH.sub.2 (3-CF.sub.3 -Ph)                                                                 5-(3-CF.sub.3 -Ph)                           281                                                                              5-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                        5-CH.sub.2 (2,4-di-Cl-Ph)                                                                   5-(2,4-di-Cl-Ph)                             282                                                                              5-(CH.sub.2).sub.6 CH.sub.3                                                           5-Pyr   5-CH.sub.2 (2,5-di-Cl-Ph)                                                                   5-(2,5-di-Cl-Ph)                             283                                                                              5-(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 Pyr                                                                        5-CH.sub.2 (3-Cl,4-F-Ph)                                                                    5-(3-Cl,4-F-Ph)                              284                                                                              5-(CH.sub.2).sub.8 CH.sub.3                                                           5-O-Pyr 5-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            5-(2-Cl,4-CF.sub.3 -Ph)                      285                                                                              5-(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 Ph                                                                         5-CH.sub.2 (2-F,5-OMe-Ph)                                                                   5-(2-F,5-OMe-Ph)                             286                                                                              5-CH(CH.sub.3).sub.2                                                                  5-Ph    5-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                5-(2,4,5-tri-Cl-Ph)                          287                                                                              5-cyclohexyl                                                                          5-O-cyclohexyl                                                                        5-CH.sub.2 (2,4-di-Cl,5-CF.sub.3 -Ph)                                                       5-(2,4-di-Cl,5-CF.sub.3 -Ph)                 288                                                                              5-O(CH.sub.2).sub.7 CH.sub.3                                                          5-O(CH.sub.2).sub.11 CH.sub.3                                                         5-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             5-(2,4-di-Cl,5-OMe-Ph)                       __________________________________________________________________________

                                      TABLE 18                                    __________________________________________________________________________    T = T-18, R.sup.3 =                                                           1          2       3             4                                            __________________________________________________________________________    289                                                                              5-CF.sub.3                                                                            5-C--(CH.sub.3)                                                                       5-CH.sub.2 (4,-Cl-Ph)                                                                       (4-Cl-Ph)                                    290                                                                              5-Br    5-O(CH.sub.2).sub.9 CH.sub.3                                                          5-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 5-(4-CF.sub.3 -Ph)                           291                                                                              5-(CH.sub.2).sub.4 CH.sub.3                                                           5-OPh   5-CH.sub.2 (3-CF.sub.3 -Ph)                                                                 5-(3-CF.sub.3 -Ph)                           292                                                                              5-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                        5-CH.sub.2 (2,4-di-Cl-Ph)                                                                   5-(2,4-di-Cl-Ph)                             293                                                                              5-(CH.sub.2).sub.6 CH.sub.3                                                           5-Pyr   5-CH.sub.2 (2,5-di-Cl-Ph)                                                                   5-(2,5-di-Cl-Ph)                             294                                                                              5-(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 Pyr                                                                        5-CH.sub.2 (3-Cl,4-F-Ph)                                                                    5-(3-Cl,4-F-Ph)                              295                                                                              5-(CH.sub.2).sub.8 CH.sub.3                                                           5-O-Pyr 5-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            5-(2-Cl,4-CF.sub.3 -Ph)                      296                                                                              5-(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 Ph                                                                         5-CH.sub.2 (2-F,5-OMe-Ph)                                                                   5-(2-F,5-OMe-Ph)                             297                                                                              5-CH(CH.sub.3).sub.2                                                                  5-Ph    5-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                5-(2,4,5-tri-Cl-Ph)                          298                                                                              5-cyclohexyl                                                                          5-O-cyclohexyl                                                                        5-CH.sub.2 (2,4-di-Cl,5-CF.sub.3 -Ph)                                                       5-(2,4-di-Cl,5-CF.sub.3 -Ph)                 299                                                                              5-O(CH.sub.2).sub.7 CH.sub.3                                                          5-O(CH.sub.2).sub.11 CH.sub.3                                                         5-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             5-(2,4-di-Cl,5-OMe-Ph)                       __________________________________________________________________________

                                      TABLE 19                                    __________________________________________________________________________    T = T-19, R.sup.3 =                                                           1          2       3             4                                            __________________________________________________________________________    300                                                                              5-CF.sub.3                                                                            5-C--(CH.sub.3).sub.3                                                                 5-CH.sub.2 (4,-Cl-Ph)                                                                       5-(4-Cl-Ph)                                  301                                                                              5-Br    5-O(CH.sub.2).sub.9 CH.sub.3                                                          5-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 5-(4-CF.sub.3 -Ph)                           302                                                                              5-(CH.sub.2).sub.4 CH.sub.3                                                           5-OPh   5-CH.sub.2 (3-CF.sub.3 -Ph)                                                                 5-(3-CF.sub.3 -Ph)                           303                                                                              5-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                        5-CH.sub.2 (2,4-di-Cl-Ph)                                                                   5-(2,4-di-Cl-Ph)                             304                                                                              5-(CH.sub.2).sub.6 CH.sub.3                                                           5-Pyr   5-CH.sub.2 (2,5-di-Cl-Ph)                                                                   5-(2,5-di-Cl-Ph)                             305                                                                              5-(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 Pyr                                                                        5-CH.sub.2 (3-Cl,4-F-Ph)                                                                    5-(3-Cl,4-F-Ph)                              306                                                                              5-(CH.sub.2).sub.8 CH.sub.3                                                           5-O-Pyr 5-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            5-(2-Cl,4-CF.sub.3 -Ph)                      307                                                                              5-(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 Ph                                                                         5-CH.sub.2 (2-F,5-OMe-Ph)                                                                   5-(2-F,5-OMe-Ph)                             308                                                                              5-CH(CH.sub.3).sub.2                                                                  5-Ph    5-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                5-(2,4,5-tri-Cl-Ph)                          309                                                                              5-cyclohexyl                                                                          5-O-cyclohexyl                                                                        5-CH.sub.2 (2,4-di-Cl,5-CF.sub.3 -Ph)                                                       5-(2,4-di-Cl,5-CF.sub.3 -Ph)                 310                                                                              5-O(CH.sub.2).sub.7 CH.sub.3                                                          5-O(CH.sub.2).sub.11 CH.sub.3                                                         5-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             5-(2,4-di-Cl,5-OMe-Ph)                       __________________________________________________________________________

                                      TABLE 20                                    __________________________________________________________________________    T = T-20, R.sup.3 =                                                           1          2       3             4                                            __________________________________________________________________________    311                                                                              5-CF.sub.3                                                                            5-C--(CH.sub.3).sub.3                                                                 5-CH.sub.2 (4,-Cl-Ph)                                                                       5-(4-Cl-Ph)                                  312                                                                              5-Br    5-O(CH.sub.2).sub.9 CH.sub.3                                                          5-CH.sub.2 (4-CF.sub.3 -Ph)                                                                 5-(4-CF.sub.3 -Ph)                           313                                                                              5-(CH.sub.2).sub.4 CH.sub.3                                                           5-OPh   5-CH.sub.2 (3-CF.sub.3 -Ph)                                                                 5-(3-CF.sub.3 -Ph)                           314                                                                              5-(CH.sub.2).sub.5 CH.sub.3                                                           5-OCH.sub.2 Ph                                                                        5-CH.sub.2 (2,4-di-Cl-Ph)                                                                   5-(2,4-di-Cl-Ph)                             315                                                                              5-(CH.sub.2).sub.6 CH.sub.3                                                           5-Pyr   5-CH.sub.2 (2,5-di-Cl-Ph)                                                                   5-(2,5-di-Cl-Ph)                             316                                                                              5-(CH.sub.2).sub.7 CH.sub.3                                                           5-CH.sub.2 Pyr                                                                        5-CH.sub.2 (3-Cl,4-F-Ph)                                                                    5-(3-Cl,4-F-Ph)                              317                                                                              5-(CH.sub.2).sub.8 CH.sub.3                                                           5-O-Pyr 5-CH.sub.2 (2-Cl,4-CF.sub.3 -Ph)                                                            5-(2-Cl,4-CF.sub.3 -Ph)                      318                                                                              5-(CH.sub.2).sub.9 CH.sub.3                                                           5-CH.sub.2 Ph                                                                         5-CH.sub.2 (2-F,5-OMe-Ph)                                                                   5-(2-F,5-OMe-Ph)                             319                                                                              5-CH(CH.sub.3).sub.2                                                                  5-Ph    5-CH.sub.2 (2,4,5-tri-Cl-Ph)                                                                5-(2,4,5-tri-Cl-Ph)                          320                                                                              5-cyclohexyl                                                                          5-O-cyclohexyl                                                                        5-CH.sub.2 (2,4-di-Cl,5-CF.sub.3 -Ph)                                                       5-(2,4-di-Cl,5-CF.sub.3 -Ph)                 321                                                                              5-O(CH.sub.2).sub.7 CH.sub.3                                                          5-O(CH.sub.2).sub.11 CH.sub.3                                                         5-CH.sub.2 (2,4-di-Cl,5-OMe-Ph)                                                             5-(2,4-di-Cl,5-OMe-Ph)                       __________________________________________________________________________

                  TABLE 21                                                        ______________________________________                                        T = T-21, R.sup.3 =                                                           1         2        3          4                                               ______________________________________                                        322  4-CF.sub.3                                                                             5-CF.sub.3                                                                             H        5-(CH.sub.2).sub.3 CH.sub.3                   322  4-Cl     5-Cl     5-CO.sub.2 Me                                                                          5-CH.sub.2 CH(CH.sub.3).sub.2                 323  4-F      5-F      5-CO.sub.2 Et                                                                          5-CH.sub.2 C(CH.sub.3).sub.3                  324  4-Br     5-Br     5-COCH.sub.3                                                                           5-CH(CH.sub.3)CH.sub.2 CH.sub.3               325  4-OMe    5-OMe    5-CH.sub.3                                                                             5-C(CH.sub.3).sub.3                           326  4-OEt    5-OEt    5-CH.sub.2 CH.sub.3                                                                    5-(CH.sub.2).sub.4 CH.sub.3                   327  4-OCF.sub.3                                                                            5-OCF.sub.3                                                                            5-CH(CH.sub.3).sub.2                                                                   5-CH.sub.2 C(CH.sub.3).sub.3                  328  4-OCHF.sub.2                                                                           5-OCHF.sub.2                                                                           5-(CH.sub.2).sub.2 CH.sub.3                                                            5-(CH.sub.2).sub.2 CH(CH.sub.3).sub.2         ______________________________________                                    

                  TABLE 22                                                        ______________________________________                                        T = T-22, R.sup.3 =                                                           1         2        3          4                                               ______________________________________                                        329  4-CF.sub.3                                                                             5-CF.sub.3                                                                             H        5-(CH.sub.2).sub.3 CH.sub.3                   330  4-Cl     5-Cl     5-CO.sub.2 Me                                                                          5-CH.sub.2 CH(CH.sub.3).sub.2                 331  4-F      5-F      5-CO.sub.2 Et                                                                          5-CH.sub.2 C(CH.sub.3).sub.3                  332  4-Br     5-Br     5-COCH.sub.3                                                                           5-CH(CH.sub.3)CH.sub.2 CH.sub.3               333  4-OMe    5-OMe    5-CH.sub.3                                                                             5-C(CH.sub.3).sub.3                           334  4-OEt    5-OEt    5-CH.sub.2 CH.sub.3                                                                    5-(CH.sub.2).sub.4 CH.sub.3                   335  4-OCF.sub.3                                                                            5-OCF.sub.3                                                                            5-CH(CH.sub.3).sub.2                                                                   5-CH.sub.2 C(CH.sub.3).sub.3                  336  4-OCHF.sub.2                                                                           5-OCHF.sub.2                                                                           5-(CH.sub.2).sub.2 CH.sub.3                                                            5-(CH.sub.2).sub.2 CH(CH.sub.3).sub.2         ______________________________________                                    

                  TABLE 23                                                        ______________________________________                                        T = T-23, R.sup.3 =                                                           1         2        3          4                                               ______________________________________                                        337  4-CF.sub.3                                                                             5-CF.sub.3                                                                             H        5-(CH.sub.2).sub.3 CH.sub.3                   338  4-Cl     5-Cl     5-CO.sub.2 Me                                                                          5-CH.sub.2 CH(CH.sub.3).sub.2                 339  4-F      5-F      5-CO.sub.2 Et                                                                          5-CH.sub.2 C(CH.sub.3).sub.3                  340  4-Br     5-Br     5-COCH.sub.3                                                                           5-CH(CH.sub.3)CH.sub.2 CH.sub.3               341  4-OMe    5-OMe    5-CH.sub.3                                                                             5-C(CH.sub.3).sub.3                           342  4-OEt    5-OEt    5-CH.sub.2 CH.sub.3                                                                    5-(CH.sub.2).sub.4 CH.sub.3                   343  4-OCF.sub.3                                                                            5-OCF.sub.3                                                                            5-CH(CH.sub.3).sub.2                                                                   5-CH.sub.2 C(CH.sub.3).sub.3                  344  4-OCHF.sub.2                                                                           5-OCHF.sub.2                                                                           5-(CH.sub.2).sub.2 CH.sub.3                                                            5-(CH.sub.2).sub.2 CH(CH.sub.3).sub.2         ______________________________________                                    

                  TABLE 25                                                        ______________________________________                                        T = T-24, R.sup.3 =                                                                     2        3          4                                               ______________________________________                                        345  4-CF.sub.3                                                                             5-CF.sub.3                                                                             H        5-(CH.sub.2).sub.3 CH.sub.3                   346  4-Cl     5-Cl     5-CO.sub.2 Me                                                                          5-CH.sub.2 CH(CH.sub.3).sub.2                 347  4-F      5-F      5-CO.sub.2 Et                                                                          5-CH.sub.2 C(CH.sub.3).sub.3                  348  4-Br     5-Br     5-COCH.sub.3                                                                           5-CH(CH.sub.3)CH.sub.2 CH.sub.3               349  4-OMe    5-OMe    5-CH.sub.3                                                                             5-C(CH.sub.3).sub.3                           350  4-OEt    5-OEt    5-CH.sub.2 CH.sub.3                                                                    5-(CH.sub.2).sub.4 CH.sub.3                   351  4-OCF.sub.3                                                                            5-OCF.sub.3                                                                            5-CH(CH.sub.3).sub.2                                                                   5-CH.sub.2 C(CH.sub.3).sub.3                  352  4-OCHF.sub.2                                                                           5-OCHF.sub.2                                                                           5-(CH.sub.2).sub.2 CH.sub.3                                                            5-(CH.sub.2).sub.2 CH(CH.sub.3).sub.2         ______________________________________                                    

                  TABLE 25                                                        ______________________________________                                        T = T-25, R.sup.3 =                                                           1         2        3          4                                               ______________________________________                                        353  4-CF.sub.3                                                                             5-CF.sub.3                                                                             H        5-(CH.sub.2).sub.3 CH.sub.3                   354  4-Cl     5-Cl     5-CO.sub.2 Me                                                                          5-CH.sub.2 CH(CH.sub.3).sub.2                 355  4-F      5-F      5-CO.sub.2 Et                                                                          5-CH.sub.2 C(CH.sub.3).sub.3                  356  4-Br     5-Br     5-COCH.sub.3                                                                           5-CH(CH.sub.3)CH.sub.2 CH.sub.3               357  4-OMe    5-OMe    5-CH.sub.3                                                                             5-C(CH.sub.3).sub.3                           358  4-OEt    5-OEt    5-CH.sub.2 CH.sub.3                                                                    5-(CH.sub.2).sub.4 CH.sub.3                   359  4-OCF.sub.3                                                                            5-OCF.sub.3                                                                            5-CH(CH.sub.3).sub.2                                                                   5-CH.sub.2 C(CH.sub.3).sub.3                  360  4-OCHF.sub.2                                                                           5-OCHF.sub.2                                                                           5-(CH.sub.2).sub.2 CH.sub.3                                                            5-(CH.sub.2).sub.2 CH(CH.sub.3).sub.2         ______________________________________                                    

                  TABLE 26                                                        ______________________________________                                        T = T-26, R.sup.3 =                                                           1         2        3          4                                               ______________________________________                                        361  4-CF.sub.3                                                                             5-CF.sub.3                                                                             H        5-(CH.sub.2).sub.3 CH.sub.3                   362  4-Cl     5-Cl     5-CO.sub.2 Me                                                                          5-CH.sub.2 CH(CH.sub.3).sub.2                 363  4-F      5-F      5-CO.sub.2 Et                                                                          5-CH.sub.2 C(CH.sub.3).sub.3                  364  4-Br     5-Br     5-COCH.sub.3                                                                           5-CH(CH.sub.3)CH.sub.2 CH.sub.3               365  4-OMe    5-OMe    5-CH.sub.3                                                                             5-C(CH.sub.3).sub.3                           366  4-OEt    5-OEt    5-CH.sub.2 CH.sub.3                                                                    5-(CH.sub.2).sub.4 CH.sub.3                   367  4-OCF.sub.3                                                                            5-OCF.sub.3                                                                            5-CH(CH.sub.3).sub.2                                                                   5-CH.sub.2 C(CH.sub.3).sub.3                  368  4-OCHF.sub.2                                                                           5-OCHF.sub.2                                                                           5-(CH.sub.2).sub.2 CH.sub.3                                                            5-(CH.sub.2).sub.2 CH(CH.sub.3).sub.2         ______________________________________                                    

                                      TABLE 27                                    __________________________________________________________________________    T = T-27, R.sup.3 =                                                           1        2      3         4                                                   __________________________________________________________________________    369 2-CF.sub.3                                                                         H      2-CH.sub.3                                                                              2-CH.sub.2 C(CH.sub.3).sub.3                        370 2-Cl 2-OCF.sub.3                                                                          2-CH.sub.2 CH.sub.3                                                                     2-CH(CH.sub.3)CH.sub.2 CH.sub.3                     371 2-F  2-OCHF.sub.2                                                                         2-(CH.sub.2).sub.2 CH.sub.3                                                             2-C(CH.sub.3).sub.3                                 372 2-Br 2-CO.sub.2 Me                                                                        2-CH(CH.sub.3).sub.2                                                                    2-(CH.sub.2).sub.4 CH.sub.3                         373 2-OMe                                                                              2-CO.sub.2 Et                                                                        2-(CH.sub.2).sub.3 CH.sub.3                                                             2-CH.sub.2 C(CH.sub.3).sub.3                        374 2-OEt                                                                              2-COCH.sub.3                                                                         2-CH.sub.2 CH(CH.sub.3).sub.2                                                           2-(CH.sub.2).sub.2 CH(CH.sub.3).sub.2               __________________________________________________________________________

                                      TABLE 28                                    __________________________________________________________________________    T = T-28, R.sup.3 =                                                           1        2      3         4                                                   __________________________________________________________________________    375 2-CF.sub.3                                                                         H      2-CH.sub.3                                                                              2-CH.sub.2 C(CH.sub.3).sub.3                        376 2-Cl 2-OCF.sub.3                                                                          2-CH.sub.2 CH.sub.3                                                                     2-CH(CH.sub.3)CH.sub.2 CH.sub.3                     377 2-F  2-OCHF.sub.2                                                                         2-(CH.sub.2).sub.2 CH.sub.3                                                             2-C(CH.sub.3).sub.3                                 378 2-Br 2-CO.sub.2 Me                                                                        2-CH(CH.sub.3).sub.2                                                                    2-(CH.sub.2).sub.4 CH.sub.3                         379 2-OMe                                                                              2-CO.sub.2 Et                                                                        2-(CH.sub.2).sub.3 CH.sub.3                                                             2-CH.sub.2 C(CH.sub.3).sub.3                        380 2-OEt                                                                              2-COCH.sub.3                                                                         2-CH.sub.2 CH(CH.sub.3).sub.2                                                           2-(CH.sub.2).sub.2 CH(CH.sub.3).sub.2               __________________________________________________________________________

                                      TABLE 29                                    __________________________________________________________________________    T = T-29, R.sup.3 =                                                           1        2      3         4                                                   __________________________________________________________________________    381 2-CF.sub.3                                                                         H      2-CH.sub.3                                                                              2-CH.sub.2 C(CH.sub.3).sub.3                        382 2-Cl 2-OCF.sub.3                                                                          2-CH.sub.2 CH.sub.3                                                                     2-CH(CH.sub.3)CH.sub.2 CH.sub.3                     383 2-F  2-OCHF.sub.2                                                                         2-(CH.sub.2).sub.2 CH.sub.3                                                             2-C(CH.sub.3).sub.3                                 384 2-Br 2-CO.sub.2 Me                                                                        2-CH(CH.sub.3).sub.2                                                                    2-(CH.sub.2).sub.4 CH.sub.3                         385 2-OMe                                                                              2-CO.sub.2 Et                                                                        2-(CH.sub.2).sub.3 CH.sub.3                                                             2-CH.sub.2 C(CH.sub.3).sub.3                        386 2-OEt                                                                              2-COCH.sub.3                                                                         2-CH.sub.2 CH(CH.sub.3).sub.2                                                           2-(CH.sub.2).sub.2 CH(CH.sub.3).sub.2               __________________________________________________________________________

                                      TABLE 30                                    __________________________________________________________________________    T = T-30, R.sup.3 =                                                           1        2      3         4                                                   __________________________________________________________________________    387 2-CF.sub.3                                                                         H      2-CH.sub.3                                                                              2-CH.sub.2 C(CH.sub.3).sub.3                        388 2-Cl 2-OCF.sub.3                                                                          2-CH.sub.2 CH.sub.3                                                                     2-CH(CH.sub.3)CH.sub.2 CH.sub.3                     389 2-F  2-OCHF.sub.2                                                                         2-(CH.sub.2).sub.2 CH.sub.3                                                             2-C(CH.sub.3).sub.3                                 390 2-Br 2-CO.sub.2 Me                                                                        2-CH(CH.sub.3).sub.2                                                                    2-(CH.sub.2).sub.4 CH.sub.3                         391 2-OMe                                                                              2-CO.sub.2 Et                                                                        2-(CH.sub.2).sub.3 CH.sub.3                                                             2-CH.sub.2 C(CH.sub.3).sub.3                        392 2-OEt                                                                              2-COCH.sub.3                                                                         2-CH.sub.2 CH(CH.sub.3).sub.2                                                           2-(CH.sub.2).sub.2 CH(CH.sub.3).sub.2               __________________________________________________________________________

                  TABLE 31                                                        ______________________________________                                        T = T-31, G = O, m = 1 or 2, R.sup.6 =                                        1             2         3         4                                           ______________________________________                                        393     6-H       6,6-diMe  6,6-diEt                                                                              6-Me,6-Et                                 394     7,7-diMe  8,8-diMe  6-Me    6-nBu                                     395     6-H       6,6-diMe  6,6-diEt                                                                              6-Me,6-Et                                 396     7,7-diMe  8,8-diMe  6-Me    6-nBu                                     397     6-H       6,6-diMe  6,6-diEt                                                                              6-Me,6-Et                                 398     7,7-diMe  8,8-diMe  6-Me    6-nBu                                     ______________________________________                                    

                  TABLE 32                                                        ______________________________________                                        T = T-32, G = O, m = 1 or 2, R.sup.6 =                                        1           2          3         4                                            ______________________________________                                        399     5-H     5,5-diMe   5,5-diEt                                                                              5-Me,5-Et                                  400     5-H     5,5-diMe   5,5-diEt                                                                              5-Me,5-Et                                  ______________________________________                                    

                  TABLE 33                                                        ______________________________________                                        T = T-33, G = O, m = 1 or 2, R.sup.6 =                                        1           2          3         4                                            ______________________________________                                        401     5-H     5,5-diMe   5,5-diEt                                                                              5-Me,5-Et                                  402     5-H     5,5-diMe   5,5-diEt                                                                              5-Me,5-Et                                  ______________________________________                                         Formulation/Utility

Compounds of this invention will generally be used in formulation withan agriculturally suitable carrier comprising a liquid or solid diluent.Useful formulations include dusts, granules, baits, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates, dryflowables and the like, consistent with the physical properties of theactive ingredient, mode of application and environmental factors such assoil type, moisture and temperature. Sprayable formulations can beextended in suitable media and used at spray volumes from about one toseveral hundred liters per hectare. High strength compositions areprimarily used as intermediates for further formulation. Theformulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up 100 weight percent.

    ______________________________________                                                     Weight Percent                                                                Active                                                                        Ingredient                                                                            Diluent   Surfactant                                     ______________________________________                                        Wettable Powders                                                                              5-90      0-74     1-10                                       Oil Suspensions, Emulsions                                                                    5-50     40-95     0-15                                       Solutions, (including                                                         Emulsifiable Concentrates)                                                    Dusts           1-25     70-99     0-5                                        Granules, Baits and Pellets                                                                  0.01-99      5-99.99                                                                              0-15                                       High Strength  90-99      0-10     0-2                                        Compositions                                                                  ______________________________________                                    

Typical solid diluents are described in Watkins, et al., Handbook ofInsecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books,Caldwell, N.J. Typical liquid diluents and solvents are described inMarsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp.,Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of SurfaceActive Agents, Chemical Publ. Co., Inc., New York, 1964, listsurfactants and recommended uses. All formulations can contain minoramounts of additives to reduce foam, caking, corrosion, microbiologicalgrowth, and the like.

Solutions are prepared by simply mixing the ingredients. Fine solidcompositions are made by blending and, usually, grinding as in a hammermill or fluid energy mill. Water-dispersible granules can be produced byagglomerating a fine powder composition; see for example, Cross et al.,Pesticide Formulations, Washington, D.C., 1988, pp 251-259. Suspensionsare prepared by wet-milling; see, for example, U.S. Pat. No. 3,060,084.Granules and pellets can be made by spraying the active material uponpreformed granular carriers or by agglomeration techniques. SeeBrowning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp147-148, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, NewYork, 1963, pages 8-57 and following, and WO 91/13546.

For further information regarding the art of formulation, see U.S. Pat.3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41;U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 andExamples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138 -140, 162-164, 166, 167and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5,line 17 and Examples 1-4; Klingman, Weed Control as a Science, JohnWiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., WeedControl Handbook, 8th Ed., Blackwell Scientific Publications, Oxford,1989.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Table A.

    ______________________________________                                        Example A                                                                     Wettable Powder                                                               Compound 1              65.0%                                                 dodecylphenol polyethylene glycol ether                                                               2.0%                                                  sodium ligninsulfonate  4.0%                                                  sodium silicoaluminate  6.0%                                                  montmorillonite (calcined)                                                                            23.0%.                                                Example B                                                                     Granule                                                                       Compound 1              10.0%                                                 attapulgite granules (low volatile                                                                    90.0%.                                                matter, 0.71/0.30 mm; U.S.S. No.                                              25-50 sieves)                                                                 Example C                                                                     Extruded Pellet                                                               Compound 1              25.0%                                                 anhydrous sodium sulfate                                                                              10.0%                                                 crude calcium ligninsulfonate                                                                         5.0%                                                  sodium alkylnaphthalenesulfonate                                                                      1.0%                                                  calcium/magnesium bentonite                                                                           59.0%.                                                Example D                                                                     Emulsifiable Concentrate                                                      Compound 1              20.0%                                                 blend of oil soluble sulfonates                                                                       10.0%                                                 and polyoxyethylene ethers                                                    isophorone              70.0%.                                                ______________________________________                                    

The compounds of this invention exhibit activity against a wide spectrumof foliar-feeding, fruit-feeding, stem or root feeding, seed-feeding,aquatic and soil-inhabiting arthropods (term "arthropods" includesinsects, mites and nematodes) which are pests of growing and storedagronomic crops, forestry, greenhouse crops, ornamentals, nursery crops,stored food and fiber products, livestock, household, and public andanimal health. Those skilled in the art will appreciate that not allcompounds are equally effective against all growth stages of all pests.Nevertheless, all of the compounds of this invention display activityagainst pests that include: eggs, larvae and adults of the OrderLepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding,seed-feeding larvae and adults of the Order Coleoptera; eggs, immaturesand adults of the Orders. Hemiptera and Homoptera; eggs, larvae, nymphsand adults of the Order Acari; eggs, immatures and adults of the OrdersThysanoptera, Orthoptera and Dermaptera; eggs, immatures and adults ofthe Order Diptera; and eggs, juveniles and adults of the PhylumNematoda. The compounds of this invention are also active against pestsof the Orders Hymenoptera, Isoptera, Siphonaptera, Blattaria, Thysanuraand Psocoptera; pests belonging to the Class Arachnida and PhylumPlatyhelminthes. Specifically, the compounds are active against southerncorn rootworm (Diabrotica undecimpunctata howardi), aster leafhopper(Mascrosteles fascifrons), boll weevil (Anthonomus grandis), two-spottedspider mite (Tetranychus urticae), fall armyworm (Spodopterafrugiperda),black bean aphid (Aphisfabae), tobacco budworm (Heliothis virescens),rice water weevil (Lissorhoptrus oryzophilus), rice leaf beetle (Oulemaoryzae), whitebacked planthopper (Sogatellafurcifera), green leafhopper(Nephotettix cincticeps), brown planthopper (Nilaparvata lugens), smallbrown planthopper (Laodelphax striatellus), rice stem borer (Chilosugpressalis), rice leafroller (Cnaphalocrocis medinalis), black ricestink bug (Scotinophara lurida), rice stink bug (Oebalus pugnax), ricebug (Leptocorisa chinensis), slender rice bug (Cletus puntiger), andsouthern green stink bug (Nezara viridula). The compounds are active onmites, demonstrating ovicidal, larvicidal and chemosterilant activityagainst such families as Tetranychidae including Tetranychus urticae,Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus,Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi, Panonychuscitri, Eotetranychus carpini borealis, Eotetranychus, hicoriae,Eotetranychus sexrnaculatus, Eotetranychus yumensis, Eotetranychusbanksi and Oligonychus pratensis; Tenuipalpidae including Brevipalpuslewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpusobovatus; Eriophyidae including Phyllocoptruta oleivora, Eriophyessheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae.See WO 90/10623 and WO 92/00673 for more detailed pest descriptions.

Compounds of this invention can also be mixed with one or more otherinsecticides, fungicides, nematocides, bactericides, acaricides, growthregulators, chemosterilants, semiochemicals, repellents, attractants,pheromones, feeding stimulants or other biologically active compounds toform a multi-component pesticide giving an even broader spectrum ofagricultural protection. Examples of other agricultural protectants withwhich compounds of this invention can be formulated are: insecticidessuch as avermectin B, monocrotophos, carbofuran, tetrachlorvinphos,malathion, parathion-methyl, methomyl, chlordimeform, diazinon,deltamethrin, oxamyl, fenvalerate, esfenvalerate, permethrin,profenofos, sulprofos, trifiumuron, difiubenzuron, methoprene,buprofezin, thiodicarb, acephate, azinphosmethyl, chlorpyrifos,dimethoate, fipronil, fiufenprox, fonophos, isofenphos, methidathion,metha-midophos, phosmet, phosphamidon, phosalone, pirimicarb, phorate,terbufos, trichlorfon, methoxychlor, bifenthrin, biphenate, cyfiuthrin,tefiuthrin, fenpropathrin, fiuvalinate, fiucythrinate, tralomethrin,imidacloprid, metaldehyde and rotenone; fungicides such as carbendazim,thiuram, dodine, maneb, chloroneb, benomyl, cymoxanil, fenpropidine,fenpropimorph, triadimefon, captan, thiophanate-methyl, thiabendazole,phosethyl-Al, chlorothalonil, dichloran, metalaxyl, captafol, iprodione,oxadixyl, vinclozolin, kasugamycin, myclobutanil, tebuconazole,difenoconazole, diniconazole, fluquinconazole, ipconazole, metconazole,penconazole, propiconazole, uniconzole, flutriafol, prochloraz,pyrifenox, fenarimol, triadimenol, diclobutrazol, copper oxychloride,furalaxyl, folpet, flusilazol, blasticidin S, diclomezine, edifenphos,isoprothiolane, iprobenfos, mepronil, neo-asozin, pencycuron,probenazole, pyroquilon, tricyclazole, validamycin, and flutolanil;nematocides such as aldoxycarb, fenamiphos and fosthietan; bactericidessuch as oxytetracyline, streptomycin and tribasic copper sulfate;acaricides such as binapacryl, oxythioquinox, chlorobenzilate, dicofol,dienochlor, cyhexatin, hexythiazox, amitraz, propargite, tebufenpyradand fenbutatin oxide; and biological agents such as entomopathogenicbacteria, virus and fungi.

In certain instances, combinations with other arthropodicides having asimilar spectrum of control but a different mode of action will beparticularly advantageous for resistance management.

Arthropod pests are controlled and protection of agronomic,horticultural and specialty crops, animal and human health is achievedby applying one or more of the compounds of this invention, in aneffective amount, to the environment of the pests including theagronomic and/or nonagronomic locus of infestation, to the area to beprotected, or directly on the pests to be controlled. Thus, the presentinvention further comprises a method for the control of foliar and soilinhabiting arthropods and nematode pests and protection of agronomicand/or nonagronomic crops, comprising applying one or more of thecompounds of Formula I, or compositions containing at least one suchcompound, in an effective amount, to the environment of the pestsincluding the agronomic and/or nonagronomic locus of infestation, to thearea to be protected, or directly on the pests to be controlled. Apreferred method of application is by spraying. Alternatively, granularformulations of these compounds can be applied to the plant foliage orthe soil. Other methods of application include direct and residualsprays, aerial sprays, seed coats, microencapsulations, systemic uptake,baits, eartags, boluses, foggers, fumigants, aerosols, dusts and manyothers. The compounds can be incorporated into baits that are consumedby the arthropods or in devices such as traps and the like.

The compounds of this invention can be applied in their pure state, butmost often application will be of a formulation comprising one or morecompounds with suitable carriers, diluents, and surfactants and possiblyin combination with a food depending on the contemplated end use. Apreferred method of application involves spraying a water dispersion orrefined oil solution of the compounds. Combinations with spray oils,spray oil concentrations, spreader stickers, adjuvants, and synergistsand other solvents such as piperonyl butoxide often enhance compoundefficacy.

The rate of application required for effective control will depend onsuch factors as the species of arthropod to be controlled, the pest'slife cycle, life stage, its size, location, time of year, host crop oranimal, feeding behavior, mating behavior, ambient moisture,temperature, and the like. Under normal circumstances, application ratesof about 0.01 to 2 kg of active ingredient per hectare are sufficient tocontrol pests in agronomic ecosystems, but as little as 0.001 kg/hectaremay be sufficient or as much as 8 kg hectare may be required. Fornonagronomic applications, effective use rates will range from about 1.0to 50 mg/square meter but as little as 0.1 mg/square meter may besufficient or as much as 150 mg/square meter may be required.

The following TESTS demonstrate the control efficacy of compounds ofthis invention on specific pests. The pest control protection affordedby the compounds is not limited, however, to these species. See IndexTable A for compound descriptions.

                  INDEX TABLE A                                                   ______________________________________                                         ##STR18##                                                                    Com-                                 Physical                                 pound R.sup.1                                                                             R.sup.2                                                                             Q                  Properties                               ______________________________________                                         1    F     F                                                                                    ##STR19##         oil (a)                                   2    F     F                                                                                    ##STR20##         oil (b)                                   3    F     Cl                                                                                   ##STR21##         oil (c)                                   4    F     Cl                                                                                   ##STR22##         oil (d)                                   5    F     Cl                                                                                   ##STR23##         oil (e)                                   6    Cl    Cl                                                                                   ##STR24##         oil (f)                                   7    F     H                                                                                    ##STR25##         oil (g)                                   8    F     F                                                                                    ##STR26##         oil (h)                                   9    F     F                                                                                    ##STR27##         oil (i)                                  10    Cl    H                                                                                    ##STR28##         oil (j)                                  11    F     F                                                                                    ##STR29##         oil (k)                                  12    F     F                                                                                    ##STR30##         mp 117- 118° C.                   13    F     F                                                                                    ##STR31##         oil (l)                                  14    F     F                                                                                    ##STR32##         oil (m)                                  15    F     F                                                                                    ##STR33##         oil (n)                                  16    F     F                                                                                    ##STR34##         oil (o)                                  17    F     F                                                                                    ##STR35##         oil (p)                                  18    F     F                                                                                    ##STR36##         oil (q)                                  19    F     F                                                                                    ##STR37##         oil (r)                                  20    F     F                                                                                    ##STR38##         mp 68- 70° C.                     21    F     F                                                                                    ##STR39##         mp 64- 58° C.:                    22    F     F                                                                                    ##STR40##         semi- solid (s)                          23    F     F                                                                                    ##STR41##         mp 96- 98° C.                     24    F     F                                                                                    ##STR42##         oil (t)                                  25    F     F                                                                                    ##STR43##         oil (u)                                  26    F     F                                                                                    ##STR44##         oil (v)                                  27    F     F                                                                                    ##STR45##         oil (w)                                  28    F     Cl                                                                                   ##STR46##         mp 117- 118° C.                   29    Cl    Cl                                                                                   ##STR47##         mp 125- 127° C.                   30    F     F                                                                                    ##STR48##         oil (x)                                  31    F     F                                                                                    ##STR49##         mp 88- 90° C.                     32    F     F                                                                                    ##STR50##         mp 75- 76° C.                     ______________________________________                                         .sup.1 H NMR data for compounds in Table A (CDCl.sub.3, 200 MHz, δ)     (a) 7.4-7.0 (6H), 5.4 (1H), 4.8 (1H), 4.3 (1H), 2.8 (4H), 1.8 (4H)            (b) 8.0-7.1 (10H), 5.6 (1H), 4.9 (1H), 4.4 (1H)                               (c) 8.0-7.0 (10H), 5.65 (1H), 4.9 (1H), 4.4 (1H)                              (d) 8.0-7.1 (10H), 5.65 (1H), 4.9.(1H), 4.4 (1H)                              (e) 7.4-7.0 (6H), 5.4 (1H), 4.8 (1H), 4.3 (1H), 2.8 (4H), 1.8 (4H)            (f) 7.4-7.1 (6H), 5.5 (1H), 4.8 (1H), 4.3 (1H), 2.8 (4H), 1.8 (4H)            (g) 8.0-7.1 (7H), 5.4 (1H), 4.8 (1H), 4.3 (1H), 2.8 (4H), 1.8 (4H)            (h) 7.3-6.7 (6H), 5.4 (1H), 4.8 (1H), 4.3 (1H), 1.6 (6H)                      (i) 7.4-7.0 (6H) 3 5.4 (1H), 4.8 (1H), 4.1 (1H), 2.9 (4H), 2.0 (2H)           (j) 8.0-7.0 (7H), 5.4 (1 H), 4.8 (1H), 4.3 (1H), 2.8 (4H), 1.8 (4H)           (k) 7.4-6.8 (6H), 5.4 (1H), 4.8 (1H), 4.3 (1H), 4.2 (4H)                      (l) 7.70 (1H), 7.30 (2H), 7.15 (1H), 6.95 (1H), 5.70 (1H), 4.80 (1H), 4.3     (1H)                                                                          (m) 7.20-6.90 (10H), 5.70 (1H), 4.80 (1H), 4.45 (1H)                          (n) 7.79 (2H), 7.45 (2H), 7.25 (1H), 7.10 (3H), 5.70 (1H), 4.82 (1H), 4.4     (1H)                                                                          (o) 7.46 (3H), 7.25 (2H), 7.00 (3H), 5.70 (1H), 4.81 (1H), 4.40 (1H)          (p) 7.61 (1H), 7.44 (2H), 7.13 (2H), 7.00 (3H), 5.70 (1H), 4.82 (1H), 4.4     (1H)                                                                          (q) 7.43 (3H), 7.24 (2H), 6.99 (3H), 5.70 (1H), 4.82 (1H), 4.30 (1H)          (r) 7.50 (2H), 7.41 (1H), 7.08 (1H), 6.98 (3H), 6.90 (2H), 5.70 (1H), 4.8     (1H), 4.85 (1H), 3.83 (3H)                                                    (s) 7.64-6.99 (9H), 5.70 (1H), 4.82 (1H), 4.43 (1H)                           (t) 7.58-6.98 (9H), 5.69 (1H), 4.80 (1H), 4.42 (1H)                           (u) 7.41-6.60 (10H), 5.60 (1H), 4.75 (1H), 4.34 (1H), 4.10 (2H)               (v) 7.40-6.64 (5H), 5.62 (1H), 4.76 (1H), 4.40 (1H), 2.76 (2H), 1.68 (2H)     1.20 (10H), 0.86 (3H)                                                         (w) 7.21-6.70 (5H), 5.65 (1H), 4.78 (1H), 4.41 (1H), 1.36 (9H)                (x) 7.42-6.95 (6H), 5.72 (1H), 4.80 (1H), 4.41 (1H)                      

TEST A

Two-Spotted Spider Mite (Tetranychus urticae)

A solution of the test compound was prepared by dissolving it in aminimum of acetone and then adding water containing a wetting agentuntil the concentration of Compound 1 was 50 ppm. Two-week old redkidney bean plants infested with two-spotted spider mites eggs weresprayed to run-off with the test solution using a turntable sprayer.Plants were held in a chamber at 25° C. and 50% relative humidity. Ofthe compounds tested, the following gave mortality levels of 80% orhigher seven days after spraying: 1, 2*, 3*, 4*, 5, 6, 7, 8, 9, 11, 12,13, 14, 15, 16, 17, 18, 20*, 21, 22, 23, 24, 25, 27, 28, 29.

TEST B

Fall Armyworm

Test units, each consisting of a H.I.S. (high impact styrene) trays with16 cells were prepared. In 12 of the cells, wet filter paper andapproximately 8 cm² of lima leaf were placed, in the other 4 cells wasplaced a 0.5 cm layer of wheat germ diet. Fifteen to twenty third instarlarvae of fall armyworm (Spodoptera frugiperda) were placed in a 8 ounce(230 mL) plastic cup. Solutions of each of the test compounds in 75/25acetone/distilled water solvent were sprayed into the tray and cup.Spraying was accomplished by passing the tray and cup, on a conveyorbelt, directly beneath a flat fan hydraulic nozzle which discharged thespray at a rate of 0.125 pounds of active ingredient per acre (about0.137 kg/ha) at 30 psi (207 kPa). The insects were transferred into thetray (one insect per cell). The trays were covered and held at 27° C.and 50% relative humidity for 48 hours after which time readings weretaken on the 12 cells with lima leaves. The 4 remaining cells were readat 7 days for a delayed toxicity reading. Of the compounds tested, thefollowing gave mortality levels of 80% or higher at the 7 day reading:15, 16, 17, 21, 22, 23*.

We claim:
 1. A compound of the formula ##STR51## wherein: A is selected from the group a direct bond and C₁ -C₃ straight or branched chain alkylene;E is selected from the group C₁ -C₄ alkyl and C₁ -C₄ haloalkyl; Z is selected from the group O and S; q is 0, 1, 2 or 3; Q is a 5- to 16- membered aromatic ring system selected from the group:(i) monocylic aromatic ring containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur; (ii) fused carbobicyclic ring containing 8 to 12 carbons, with the proviso that when the ring is naphthyl and is on the oxazoline ring carbon adjacent to the oxazoline ring oxygen, and when E is CH₃ and q is 1, then R¹ is other than H; (iii) fused carbotricyclic ring containing 12 to 16 carbons; (iv) fused bicylic ring containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur; (v) fused tricylic ring containing 1 to 6 heteroatoms independently selected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur; and (vi) phenyl substituted with M-J¹ ; Q being substituted with 1 to 6 substituents selected independently from the group R³, R⁴, (R⁵) and (R⁶)_(m) ; R¹ and R² are independently selected from the group H, halogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy, C₁ -C₆ alkylthio, CN and NO₂ ; R³ and R⁵ are independently selected from the group H, halogen, C₁ -C₁₆ alkyl, C₁ -C₁₆ haloalkyl, C₃ -C₇ cycloalkyl, C₄ -C₁₆ cycloalkylalkyl, C₂ -C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl, C₂ -C₁₆ alkynyl, C₂ -C₁₆ haloalkynyl, C₂ -C₁₆ alkoxyalkoxy, OR⁷, R⁷ OC(O)--, R⁷ C(O)--, Si(R¹³)(R¹⁴)R¹⁵ and M-J; R⁴ is selected from the group H, halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl and C₁ -C₆ haloalkoxy; R⁶ is selected from the group H, halogen, C₁ -C₁₀ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy; and phenyl optionally substituted with R⁸ ; R⁷ is selected from the group C₃ -C₇ cycloalkyl, C₄ -C₇ cycloalkylalkyl, C₁ -C₁₆ alkyl, C₁ -C₁₆ haloalkyl, C₂ -C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl, C₂ -C₁₆ alkynyl and C₂ -C₁₆ haloalkynyl; R⁸ is selected from the group halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy and Si(R⁹)(R¹⁰)R¹¹ ; R⁹, R¹⁰ and R¹¹ are independently C₁ -C₁₂ alkyl; M is selected from the group a direct bond, S, O, C(═O), C(=O)O--C₁ -C₂ alkylene, C₁ -C₄ alkylene, O--C₁ -C₄ alkylene and O--C₂ -C₄ alkenylene, wherein when M is O--C₁ -C₄ alkylene or O--C₂ -C₄ alkenylene, the oxygen atom is attached to either ring and when M is C(═O)O--C₁ -C₂, the C(═O) is attached to either ring; J is selected from the group phenyl optionally substituted with independently selected substituents (R¹²)_(n) ; and a 5-or 6-membered aromatic ring, attached through carbon or nitrogen, containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur, the ring optionally substituted with independently selected substituents (R¹²)_(n) ; J¹ is selected from the group a 5- membered aromatic ring, attached through carbon or nitrogen, containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur, and a 6-membered ring containing 2 to 4 nitrogen atoms each ring optionally substituted with independently selected substituents (R¹²)_(n) ; R¹² is selected from the group halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy and Si(R¹³)(R¹⁴)R¹⁵ ; R¹³, R¹⁴ and R¹⁵ are independently C₁ -C₁₂ alkyl; m and n are integers independently selected from 1 to 4; and p is 1 or
 2. 2. A compound according to claim 1 wherein:Q is selected from the group ##STR52## A is selected from the group a direct bond and C₁ -C₃ straight or branched chain alkylene; G and Z are independently selected from the group O and S; W, X and Y are independently selected from the group S, O, CR³, N═CR⁷ and NR⁸ wherein only one of W, X and Y can be O, S or N═CR⁷ ; R¹ and R² are independently selected from the group H, halogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy, C₁ -C₆ alkylthio, CN and NO₂ ; R³ and R⁵ are independently selected from the group H, halogen, C₁ -C₁₆ alkyl, C₃ -C₇ cycloalkyl, C₄ -C₁₆ cycloalkylalkyl, C₁ -C₁₆ haloalkyl, C₂ -C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl, C₂ -C₁₆ alkynyl, C₂ -C₁₆ haloalkynyl, C₂ -C₁₆ alkoxyalkoxy, OR⁹, R⁹ OC(O)--, R⁹ C(O)-- and ##STR53## R⁴ and R⁷ are independently selected from the group H, halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl and C₁ -C₆ haloalkoxy; R⁶ is selected from the group H, halogen, C₁ -C₁₀ alkyl and phenyl optionally substituted with R¹⁰ ; R⁸ is selected from the group H and C₁ -C₆ alkyl; R⁹ is selected from the group C₃ -C₇ cycloalkyl, C₄ -C₇ cycloalkylalkyl, C₁ -C₁₆ alkyl, C₁ -C₁₆ haloalkyl, C₂ -C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl, C₂ -C₁₆ alkynyl and C₂ -C₁₆ haloalkynyl; R¹⁰ is selected from the group halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy and Si(R¹¹)(R¹²)R¹³ ; R¹¹, R¹² and R¹³ are independently C₁ -C₃ alkyl; J is selected from the group CH, CR¹⁰ and N; M is selected from the group a direct bond, O, C(O), C(O)O and C₁ -C₃ straight or branched chain alkylene; m is an integer from 1 to 4; n is 0 or an integer from 1 to 4; p is 1 or 2; t is 1, 2 or 3; and q is
 0. 3. A compound according to claim 1 wherein Q is selected from the group: ##STR54## G being selected from the group O and S; W, X and Y being independently selected from the group N, S, O, CR⁵, N═CR⁶ and NR¹⁶ wherein only one of W, X and Y is O, S or N═CR⁶ ;R¹⁶ being selected from the group H, C₁ -C₆ alkyl and phenyl optionally substituted with 1 to 3 substituents independently selected from the group R¹⁷ ; R¹⁷ is selected from the group C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, halogen, NO₂ and CN; and t is 1, 2 or
 3. 4. A compound according to claim 3 wherein when one of W, X or Y is S, the remaining two are not both CR⁵.
 5. A compound according to claim 3 whereinA is a direct bond; R¹ is selected from the group F and Cl in the 2-position; R² is selected from the group H, F and Cl in the 6-position; R³ and R⁵ are independently selected from the group H, halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy and M-J; and J is selected from the group phenyl, thienyl, pyridyl and furyl.
 6. A compound according to claim 5 wherein Q is selected from the group Q-1, Q-2, Q-3 and Q-4.
 7. A compound according to claim 6 wherein:Q is Q-1; W is S; X and Y are CR⁵ ; R³ is M-J; M is a direct bond; J is phenyl; R¹² is in the meta or para position and is selected from the group halogen and CF₃ ; and n is 1 or
 2. 8. A compound according to claim 6 selected from:(2-(2,6-difluorophenyl)-4-[5-(1,1-dimethylethyl)-2-thienyl]-4,5-dihydrooxazole, 4-[5-(4-chlorophenyl)-2-thienyl]-2-2-(2,6-difluorophenyl)-4,5-dihydrooxazole, and 2-(2,6-difluorophenyl)-4-(2,2-dimethyl-1,3-benzodioxol-5-yl)-4,5-dihydrooxazole.
 9. An arthropodicidal composition comprising an arthropodicidally effective amount of a compound according to any one of claims 1 to 8 and a carrier therefor.
 10. A method for controlling arthropods comprising applying to the arthropods or to their environment an arthropodicidally effective amount of a compound according to any one of claims 1 to
 8. 11. A method for controlling arthropods comprising applying to the arthropods or their environment an arthropodicidally effective amount of a compound of the formula ##STR55## wherein: A is selected from the group a direct bond and C₁ -C₃ straight or branched chain alkylene;E is selected from the group C₁ -C₄ alkyl and C₁ -C₄ haloalkyl; Z is selected from the group O and S; q is 0, 1, 2 or 3; Q is a 5- to 16- membered aromatic ring system selected from the group:(i) monocylic aromatic ring containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur; (ii) fused carbobicyclic ring containing 8 to 12 carbons; (iii) fused carbotricyclic ring containing 12 to 16 carbons; (iv) fused bicylic ring containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur; (v) fused tricylic ring containing 1 to 6 heteroatoms independently selected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur; and (vi) phenyl substituted with M-J¹ ; Q being substituted with 1 to 6 substituents selected independently from the group R³, R⁴, (R⁵)_(p) and (R⁶)_(m) ; R¹ and R² are independently selected from the group H, halogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy, C₁ -C₆ alkylthio, CN and NO₂ ; R³ and R⁵ are independently selected from the group H, halogen, C₁ -C₁₆ alkyl, C₁ -C₁₆ haloalkyl, C₃ -C₇ cycloalkyl, C₄ -C₁₆ cycloalkylalkyl, C₂ -C₁₆ alkenyl, C₂ -C₁₆ haloalkenyl, C₂ -C₁₆ alkynyl, C₂ -C₁₆ haloalkynyl, C₂ -C₁₆ alkoxyalkoxy, OR⁷, R⁷ OC(O)--, R⁷ C(O)--, Si(R¹³)(R¹⁴)R¹⁵ and M-J; R⁴ is selected from the group H, halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl and C₁ -C₆ haloalkoxy; R⁶ is selected from the group H, halogen, C₁ -C₁₀ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy; and phenyl optionally substituted with R⁸ ; R⁷ is selected from the group C₃ -C₇ cycloalkyl, C₄ -C₇ cycloalkylalkyl, C₁ -C₁₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₁₆ alkenyl; C₂ -C₁₆ haloalkenyl, C₂ -C₁₆ alkynyl and C₂ -C₁₆ haloalkynyl; R⁸ is selected from the group halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy and Si(R⁹)(R¹⁰)R¹¹ ; R⁹, R¹⁰ and R¹¹ are independently C₁ -C₁₂ alkyl; M is selected from the group a direct bond, S, O, C(═O), C(═O)O--C₁ -C₂ alkylene, C₁ -C₄ alkylene, O--C₁ -C₄ alkylene and O--C₂ -C₄ alkenylene, wherein when M is O--C₁ -C₄ alkylene or O--C₂ -C₄ alkenylene, the oxygen atom is attached to either ring and when M is C(═O)O--C₁ -C₂, the C(═O) is attached to either ring; J is selected from the group phenyl optionally substituted with independently selected substituents (R¹²)_(n) ; and a 5-or 6-membered aromatic ring, attached through carbon or nitrogen, containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur, the ring optionally substituted with independently selected substituents (R¹²)_(n) ; J¹ is selected from the group a 5-membered aromatic ring, attached through carbon or nitrogen, containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur, and a 6-membered ring containing 2 to 4 nitrogen atoms each ring optionally substituted with independently selected substituents (R¹²)_(n) ; R¹² is selected from the group halogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl, C₁ -C₆ haloalkoxy and Si(R¹³)(R¹⁴)R¹⁵ ; R¹³, R¹⁴ and R¹⁵ are independently C₁ -C₁₂ alkyl; m and n are integers independently selected from 1 to 4; and p is 1 or
 2. 